Pyrimidyl phenyl and benzyl ethers, process and intermediate products for their production and their use as herbicide

ABSTRACT

Pyrimidyl phenyl and pyrimidyl benzyl ethers of the general formula I ##STR1## and their salts and N-oxides, where the substituents and indices have the following meanings: 
     Q is (CO 2  CH 3 )═CHCH 3 , C(CO 2  CH 3 )═CHOCH 3 , C(CONHCH 3 )═CHOCH 3 , C(CONH 2 )═NOCH 3 , C(CONHCH 3 )═NOCH 3  or N(OCH 3 )--CO 2  CH 3  ; 
     n is 0 or 1; 
     R 1  is hydrogen or an organic radical bonded via a carbon atom; 
     R 2  is hydrogen, cyano, halogen or an organic radical bonded via a carbon, oxygen, sulfur or nitrogen atom; 
     R 3  is hydrogen, halogen, C 1  -C 4  -alkyl or C 1  -C 2  -haloalkyl; 
     R 4  is hydrogen, cyano, nitro, halogen or an organic radical bonded via a carbon, oxygen, sulfur or nitrogen atom; 
     y is 0, 1, 2 or 3, it being possible for the radicals R 5  to be different if y is 2 or 3; 
     R 5  is cyano, halogen, C 1  -C 4  -alkyl, C 1  -C 4  -haloalkyl or C 1  -C 4  -alkoxy, processes and intermediates for their preparation, and their use.

DESCRIPTION

The present invention relates to pyrimidyl phenyl and pyrimidyl benzylethers of the general formula I ##STR2## and to their salts and N-oxideswhere the substituents and indices have the following meanings:

Q is C(CO₂ CH₃)═CHCH₃, C(CO₂ CH₃)═CHOCH₃, C(CONHCH₃)═CHOCH₃,C(CONH₂)═NOCH₃, C(CONHCH₃)═NOCH₃ or N(OCH₃) --CO₂ CH₃ ;

n is 0 or 1;

R¹ is hydrogen or an organic radical bonded via a carbon atom;

R² is hydrogen, cyano, halogen or an organic radical bonded via acarbon, oxygen, sulfur or nitrogen atom;

R³ is hydrogen, halogen, C₁ -C₄ -alkyl or C₁ -C₂ -haloalkyl;

R⁴ is hydrogen, cyano, nitro, halogen or an organic radical bonded via acarbon, oxygen, sulfur or nitrogen atom;

y is 0, 1, 2 or 3, it being possible for the radicals R⁵ to be differentif y is 2 or 3;

R⁵ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl or C₁ -C₄-alkoxy.

The invention furthermore relates to processes and intermediates for thepreparation of these compounds and to their use for controlling animalpests and harmful fungi.

Pyrimidylphenyl and -benzyl ethers having fungicidal, or fungicidal andinsecticidal, properties have been disclosed in the literature (EP-A 254426; EP-A 278 595; EP-A 299 694; EP-A 363 818; EP-A 350 691; EP-A 398692; EP-A 407 873; EP-A 477 631; EP-A 513 580; JP-A 04/182,461; WO-A93/15,046), which differ from the compounds according to the inventionby the substituents in the pyrimidyl moiety.

It was an object of the present invention to provide compounds with animproved activity and a widened spectrum of action.

We have found that this object is achieved by the compounds I defined atthe outset. We have furthermore found processes and intermediates forthe preparation of these compounds and their use for controlling animalpests and harmful fungi.

The compounds I are accessible via various routes by processes describedper se in the literature.

The construction of the group Q is disclosed, for example, in theliterature cited at the outset and is carried out in general and inparticular by the processes described therein.

Usually, a procedure is followed for the synthesis of the compounds I inwhich a pyrimidine derivative of the formula IIa is converted with aphenol or a benzyl alcohol of the formula IIIa in an inert solvent togive the corresponding ether of the formula IVa, and IVa is subsequentlyreacted with an O-substituted hydroxylamine (R¹ --O--NH₂) or a saltthereof to give I. ##STR3##

L¹ in formula IIa is a nucleophilically exchangeable leaving group, suchas halogen (eg. fluorine, chlorine, bromine or iodine) or alkyl- orarylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate,phenylsulfonate or methylphenylsulfonate).

1a) The reaction of IIa with IIIa is normally carried out in an inertsolvent at from 0° C. to 130° C., preferably 20° C. to 80° C. in thepresence of a base.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitrilessuch as acetonitrile and propionitrile, ketones such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone, and alsodimethyl sulfoxide and dimethylformamide, especially preferablytetrahydrofuran, acetonitrile, dimethyl sulfoxide and acetone. Mixturesof these can also be used.

Bases which are suitable are, generally, inorganic compounds such asalkali metal hydroxides and alkaline earth metal hydroxides, such aslithium hydroxide, sodium hydroxide, potassium hydroxide and calciumhydroxide, alkali metal oxides and alkaline earth metal oxides such aslithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkalimetal hydrides and alkaline earth metal hydrides, such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal amides, such as lithium amide, sodium amide and potassium amide,alkali metal carbonates and alkaline earth metal carbonates, such aslithium carbonate and calcium carbonate, and alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometallic compounds,in particular alkali metal alkyls, such as methyllithium, butyllithiumand phenyllithium, alkylmagnesium halides, such as methylmagnesiumchloride, and alkali metal alcoholates and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermoreorganic bases, eg. tertiary amines such as trimethylamine,triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine,substituted pyrimidines, such as collidine, lutidine and4-dimethylaminopyridine, and bicyclic amines. Substances which areespecially preferred are potassium carbonate, sodium hydride andpotassium tert-butylate. In general, the bases are employed in catalyticamounts, but they can also be used in equimolar amounts, in an excessor, if desired, as the solvent.

In general, the starting materials are reacted with each other ineguimolar amounts. It may be advantageous for the yield to employ anexcess of IIa based on IIIa.

1b) The reaction of IVa with the O-substituted hydroxylamine or the saltthereof is normally carried out in an inert solvent at from 0° C. to 80°C., preferably 20° C. to 60° C., in the presence or absence of an acidor in the presence or absence of a base if the O-substitutedhydroxylamine is liberated from its salt.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanoland tert-butanol, and also dimethyl sulfoxide, dimethylformamide andpyridine, especially preferably methanol and pyridine. Mixtures of thesecan also be used.

Bases which are suitable are, generally, inorganic compounds such asalkali metal hydroxides and alkaline earth metal hydroxides, such aslithium hydroxide, sodium hydroxide, potassium hydroxide and calciumhydroxide, alkali metal oxides and alkaline earth metal oxides such aslithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkalimetal hydrides and alkaline earth metal hydrides, such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal amides, such as lithium amide, sodium amide and potassium amide,alkali metal carbonates and alkaline earth metal carbonates, such aslithium carbonate and calcium carbonate, and alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometallic compounds,in particular alkali metal alkyls, such as methyllithium, butyllithiumand phenyllithium, alkylmagnesium halides, such as methylmagnesiumchloride, and alkali metal alcoholates and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermoreorganic bases, eg. tertiary amines such as trimethylamine,triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines, such as collidine, lutidine and4-dimethylaminopyridine, and bicyclic amines. Substances which areespecially preferred are pyridine and sodium hydroxide. The bases aregenerally employed in catalytic amounts, but they can also be used inequimolar amounts, in an excess or, if desired, as the solvent.

Acids and acidic catalysts which are used are inorganic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids, such as boron trifluoride, aluminumtrichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chlorideand zinc(II) chloride, and organic acids such as formic acid, aceticacid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.In general, the acids are employed in catalytic amounts.

In general, the starting materials are reacted with each other inequimolar amounts. It may be advantageous for the yield to employhydroxylamine or a salt thereof in an excess, based on IVa.

In a similar manner, the compounds I are obtained by first converting apyrimidine derivative of the formula IIa with an O-substitutedhydroxylamine (R¹ --O--NH₂) or a salt thereof to give the correspondingcompound of the formula Va, and subsequently reacting Va with a phenolor a benzyl alcohol of the formula IIIa in an inert solvent to give I.##STR4##

The reactions proceed in general and in particular by the methodsdescribed hereinabove.

Compounds I where n is 1 are preferably obtained by converting apyrimidine alcohol of the formula IIb with a benzyl compound of theformula IIIb in an inert solvent to give the corresponding benzyl etherof the formula IVb, and subsequently reacting IVb with an O-substitutedhydroxylamine (R¹ --O--NH₂) or a salt thereof to give I. ##STR5##

L² in formula IIIb is a nucleophilically exchangeable leaving group suchas halogen (eg. chlorine, bromine or iodine) or alkyl sulfonate or arylsulfonate (eg. methylsulfonate, trifluoromethylsulfonate,phenylsulfonate or methylphenylsulfonate).

2a) The reaction of IIb with IIIb is normally carried out in an inertsolvent at from 0° C. to 130° C., preferably 20° C. to 60° C., in thepresence of a base.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide anddimethylformamide, especially preferably tetrahydrofuran, acetonitrile,dimethyl sulfoxide and acetone. Mixtures of these can also be used.

Bases which are suitable are, generally, inorganic compounds such asalkali metal hydroxides and alkaline earth metal hydroxides, such aslithium hydroxide, sodium hydroxide, potassium hydroxide and calciumhydroxide, alkali metal oxides and alkaline earth metal oxides such aslithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkalimetal hydrides and alkaline earth metal hydrides, such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal amides, such as lithium amide, sodium amide and potassium amide,alkali metal carbonates and alkaline earth metal carbonates, such aslithium carbonate and calcium carbonate, and alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometallic compounds,in particular alkali metal alkyls, such as methyllithium, butyllithiumand phenyllithium, alkylmagnesium halides, such as methylmagnesiumchloride, and alkali metal alcoholates and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermoreorganic bases, eg. tertiary amines such as trimethylamine,triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines, such as collidine, lutidine and4-dimethylaminopyridine, and bicyclic amines. Substances which areespecially preferred are potassium carbonate, sodium hydride andpotassium tert-butylate. In general, the bases are employed in catalyticamounts, but they can also be used in equimolar amounts, in an excessor, if desired, as the solvent.

In general, the starting materials are reacted with each other inequimolar amounts. It may be advantageous for the yield to employ IIb inan excess, based on IIIb.

2b) The reaction of IVb with the O-substituted hydroxylamine or a saltthereof is carried out in general and in particular under the conditionsdescribed above under item lb.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitrites such as acetonitrile and propionitrile,alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanoland tert-butanol, and also dimethyl sulfoxide, dimethylformamide andpyridine, especially preferably methanol and pyridine. Mixtures of thesecan also be used.

Bases which are suitable are, generally, inorganic compounds such asalkali metal hydroxides and alkaline earth metal hydroxides, such aslithium hydroxide, sodium hydroxide, potassium hydroxide and calciumhydroxide, alkali metal oxides and alkaline earth metal oxides such aslithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkalimetal hydrides and alkaline earth metal hydrides, such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal amides, such as lithium amide, sodium amide and potassium amide,alkali metal carbonates and alkaline earth metal carbonates, such aslithium carbonate and calcium carbonate, and alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometallic compounds,in particular alkali metal alkyls, such as methyllithium, butyllithiumand phenyllithium, alkylmagnesium halides, such as methylmagnesiumchloride, and alkali metal alcoholates and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermoreorganic bases, eg. tertiary amines such as trimethylamine,triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines, such as collidine, lutidine and4-dimethylaminopyridine, and bicyclic amines. Substances which areespecially preferred are pyridine and sodium hydroxide. Bases aregenerally employed in catalytic amounts, but they can also be used inequimolar amounts, in an excess or, if desired, as the solvent.

Acids and acidic catalysts which are used are inorganic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids, such as boron trifluoride, aluminumtrichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chlorideand zinc(II) chloride, and organic acids such as formic acid, aceticacid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.In general, the acids are employed in catalytic amounts.

In general, the starting materials are reacted with each other inequimolar amounts. It may be advantageous for the yield to employ IIb inan excess, based on IIIb.

In a similar manner, the compounds I where n is 1 are obtained by firstconverting a pyrimidine alcohol of the formula IIb with an O-substitutedhydroxylamine (R¹ --O--NH₂) or a salt thereof to give the correspondingcompound of the formula Vb, and subsequently reacting Vb with a benzylcompound of the formula IIIb in an inert solvent to give I. ##STR6##

The reactions are carried out in general and in particular by themethods described above.

Those starting materials of the formulae IlIa and IIIb which arerequired for the preparation of the compounds I by the above-describedprocess and which have not already been disclosed in the literaturecited at the outset can be prepared in a similar manner by the processesdescribed therein.

The starting materials of the formula IIa can be obtained by reacting asuitably substituted pyrimidine of the formula VIa with an activatedcarboxylic acid of the formula VIla in an inert solvent in the presenceof an organometallic base [cf. J. Organomet. Chem. 56, (1973) 53-66;Chem. Ber. 125, (1992) 1169-1190]. ##STR7##

Y¹ in formula VIa is a halogen atom, eg. fluorine, chlorine, bromine andiodine, especially bromine and iodine.

L³ in formula VII is a halogen atom, eg. fluorine, chlorine, bromine andiodine, especially chlorine, or an amide radical or an ester radical. Acorresponding cyanide R² --C.tbd.N may also be employed in place of thecompound VIIa.

This reaction is normally carried out in an inert solvent in thepresence of an organometallic base at from -75° C. to 40° C., preferably-75° C. to 0° C.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, and alsodimethyl sulfoxide and dimethylformamide, especially preferably diethylether and tetrahydrofuran. Mixtures of the abovementioned solvents mayalso be used.

Organometallic bases which are generally suitable are organometalliccompounds, in particular alkali metal alkyls such as methyllithium,butyllithium and phenyllithium, alkylmagnesium halides such asmethylmagnesium chloride. n-butyllithium is especially preferred. Ingeneral, the bases can be used in equimolar amounts or in an excess.

In general, the starting materials are reacted with each other inequimolar amounts. It may be advantageous for the yield to employ VIIain an excess, based on VIa.

By a further method, the compounds IIa are also obtained by reacting apyrimidinecarbonyl halide of the general formula VIIIa with anorganometallic compound (R² --M; M is the equivalent of a metal ion) inan inert solvent [cf. DE-A 38 38 243; EP-A 446 872]. ##STR8##

Especially suitable as metal (M) are lithium, magnesium, copper andzinc.

L⁴ in formula VIIIa is a halogen atom, eg. fluorine, chlorine, bromineand iodine, especially chlorine.

This reaction is normally carried out in an inert solvent at from -80°C. to 20° C., preferably -75° C. to 0° C.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran especiallypreferably diethyl ether and tetrahydrofuran. Mixtures of these can alsobe used.

The starting materials are generally reacted with each other inequimolar amounts. It may be advantageous for the yield to employ theorganometallic compound in an excess, based on VIIIa.

In a further method, the compounds IIa are also obtained by converting apyrimidinecarbonyl halide of the general formula VIIIa with a malonicester of the formula IX in an inert solvent to give the correspondingtriketone VIIIb, and subsequently reacting VIIIb to give IIa [cf.Tetrahedron 48 (22), (1992) 9233]. ##STR9##

R^(y) in formulae VIIIb and IXa is the radical of a group R².

The symbols R in formulae VIIIb and IXa are C₁ -C₄ -alkyl groups, whichare independent of one another, in particular methyl and ethyl.

3a) The reaction of VIIIa and IXa is normally carried out in an inertsolvent at from 0° C. to 120° C., preferably 20° C. to 80° C. in thepresence of a base and in the presence or absence of a Lewis acid suchas magnesium chloride.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide,dimethylformamide, especially preferably toluene. Mixtures of these canalso be used.

Bases which are suitable are, generally, inorganic compounds such asalkali metal hydroxides and alkaline earth metal hydroxides, such aslithium hydroxide, sodium hydroxide, potassium hydroxide and calciumhydroxide, alkali metal oxides and alkaline earth metal oxides such aslithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkalimetal hydrides and alkaline earth metal hydrides, such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal amides such as lithium amide, sodium amide and potassium amide,alkali metal carbonates and alkaline earth metal carbonates, such aslithium carbonate and calcium carbonate, and alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometallic compounds,in particular alkali metal alkyls, such as methyllithium, butyllithiumand phenyllithium, alkylmagnesium halides such as methylmagnesiumchloride, and alkali metal alcoholates and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermoreorganic bases, eg. tertiary amines such as trimethylamine,triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines, such as collidine, lutidine and4-dimethylaminopyridine, and bicyclic amines. Especially preferredsubstances are sodium hydroxide and triethylamine. In general, the basesare employed in equimolar amounts, but they can also be used in anexcess or, if desired, as the solvent.

In general, the starting materials are reacted with each other inequimolar amounts. It may be advantageous for the yield to employ IXa inan excess based on VIIIa.

3b) The decarboxylation of VIIIb to IIa is normally carried out in aninert solvent at from 60° C. to 200° C., preferably 100° C. to 160° C.,in the presence or absence of a base.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- andp-xylene, halogenated hydrocarbons such as chlorobenzene, nitriles suchas acetonitrile and propionitrile, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethylsulfoxide and dimethylformamide, especially preferably water anddimethyl sulfoxide. Mixtures of these can also be used.

Bases which are suitable are, generally, inorganic compounds such asalkali metal hydroxides and alkaline earth metal hydroxides, such aslithium hydroxide, sodium hydroxide, potassium hydroxide and calciumhydroxide, alkali metal oxides and alkaline earth metal oxides such aslithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkalimetal hydrides and alkaline earth metal hydrides, such as lithiumhydride, sodium hydride, potassium hydride and calcium hydride, alkalimetal amides such as lithium amide, sodium amide and potassium amide,alkali metal carbonates and alkaline earth metal carbonates, such aslithium carbonate and calcium carbonate, and alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometallic compounds,in particular alkali metal alkyls, such as methyllithium, butyllithiumand phenyllithium, alkylmagnesium halides, such as methylmagnesiumchloride, and alkali metal alcoholates and alkaline earth metalalkoxides, such as sodium methoxide, sodium ethoxide, potassiumethoxide, potassium tert-butoxide and dimethoxymagnesium, furthermoreorganic bases, eg. tertiary amines such as trimethylamine,triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines, such as collidine, lutidine and4-dimethylaminopyridine, and bicyclic amines. Especially preferredsubstances are sodium hydroxide and sodium methanolate. In general, thebases are employed in catalytic amounts, but they can also be used inequimolar amounts, in an excess or, if desired, as the solvent.

The starting materials of the formula IIb are obtained by converting asuitably substituted pyrimidine derivative of the formula VIa with analcoholate (R'--O⁻ M⁺ ; R' is C₁ -C₄ -alkyl, M⁺ is the equivalent of analkali metal cation or alkaline earth metal cation, in particular sodiumor potassium) in the presence of a base to give the corresponding alkylpyrimidyl ether of the formula VIb, subsequently converting VIb by amethod similar to the above-described process (reaction of VIa) into thecorresponding ether IIc by reaction with an activated carboxylic acid ofthe formula VIIa, and subsequently cleaving IIc to give IIb. ##STR10##

4a) The etherification of VIa to VIb is normally carried out at from 0°C. to 120° C., preferably 20° C. to 80° C., in the presence of an inertsolvent.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, and also dimethyl sulfoxide anddimethylformamide, especially preferably dimethylformamide. Mixtures ofthese can also be used.

In general, the pyrimidine derivative VIa and the alcoholate are reactedwith each other in equimolar amounts. It may be advantageous for theyield to employ the alcoholate in an excess, based on VIa, or as thesolvent.

4b) The reaction of the ether VIb with the activated carboxylic acidVIIa is carried out in general and in particular under the conditionsdescribed for the preparation of the compounds IIa from the compoundsVIa.

4c) The ether cleavage of IIc to IIb is normally carried out at from 0°C. to 130° C., preferably 60° C. to 100° C., in an inert solvent in thepresence of a base.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, nitriles such as acetonitrileand propionitrile, alcohols such as methanol, ethanol, n-propanol,isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide anddimethylformamide, especially preferably methylene chloride. Mixtures ofthese can also be used.

Acids and acidic catalysts which are used are inorganic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids such as boron trifluoride, aluminumtrichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chlorideand zinc(II) chloride, and organic acids such as formic acid, aceticacid, propionic acid, oxalic acid, citric acid and trifluoroacetic acid.In general, the acids are employed in catalytic amounts, but they canalso be used in equimolar amounts, in an excess, or, if desired, as thesolvent.

Moreover, the intermediates of the formula IVa can be obtained byreacting an ether of the formula Xa either

(a) with an activated carboxylic acid of the formula VIIb in an inertsolvent in the presence of an organometallic base or

(b) with an organotin compound of the formula XI in an inert solvent.##STR11##

Y¹ in formula Xa is a halogen atom, such as fluorine, chlorine, bromineand iodine, in particular bromine and iodine.

Y² in formula VIIb is a halogen atom such as fluorine, chlorine, bromineand iodine, in particular chlorine.

The radicals R^(x) in formula XI are independent of one another and arealkyl.

5a) The reaction of the ether Xa with the activated carboxylic acid VIIbis carried out in general and in particular under the conditionsdescribed for the preparation of the compounds IIa from the compoundsVIa.

5b) The reaction of the ether Xa with the organotin compound XI isnormally carried out at from -70° C. to 40° C., preferably -70° C. to 0°C. in an inert solvent in the presence of a catalyst such as Pd[P(C₆H₅)₃ ]₃ and PdCl₂.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitritessuch as acetonitrile and propionitrile, and also dimethyl sulfoxide anddimethylformamide, especially preferably tetrahydrofuran and diethylether. Mixtures of these can also be used.

In general, the starting materials are reacted with each other inequimolar amounts. It may be advantageous for the yield to employ theorganotin compound XI in an excess, based on the ether Xa.

The intermediates of the formula Vc are preferably obtained bynitrozating an alkyl pyrimidyl ether VIIIe to give Vd and subsequentlyreacting Vd with a reagent R¹ --Y⁵ to give Vc. ##STR12##

Y⁵ is a nucleophilically exchangeable leaving group such as halogen (eg.fluorine, chlorine, bromine or iodine) or alkyl- or arylsulfonate (eg.methylsulfonate, trifluoromethylsulfonate, phenylsulfonate ormethylphenylsulfonate).

6a) The nitrozation of VIIIe to Vd is normally carried out in generaland in particular following the processes described in the literature[cf. Houben-Weyl, E14b, Part 1, page 287 et seq. and Liebigs Ann. Chem.737 (1970), 39].

6b) The etherification of Vd to Vc is normally carried out in generaland in particular following the processes described in the literature[cf. Houben-Weyl, E14b, Part 1, page 370 et seq.].

By a further preferred process, the compounds Vc are obtained byconverting a β-dicarbonyl of the formula XII with an amidine, guanidine,urea or thiourea of the formula XIII to give the correspondingpyrimidine VIIId', hydrolyzing VIIId' to give the ketone VIIIc andsubsequently reacting VIIIc with an O-substituted hydroxylamine (R¹--O--NH₂) or salt thereof to give I. ##STR13##

R in formula XII is an alkyl radical having 1 to 4 carbon atoms,preferably methyl or ethyl.

The symbols R^(z) in formulae XII, VIIId' and VIIIc' are alkyl groups,preferably having 1 to 4 carbon atoms, in particular methyl and ethyl;the two groups R^(z) can also together be an ethylene or propylenechain.

7a) The reaction of XII with XIII is normally carried out at from 0 to120° C., preferably 20 to 80° C., in particular at the boiling point ofthe solvent. Solvents which are normally used are alcohols, inparticular methanol or ethanol.

The compounds XIII can also be employed in the form of their salts, inparticular as hydrohalides (eg. hydrochloride or hydrobromide). If saltsare used, it is recommended to carry out the reaction in the presence ofa base (eg. alkaline earth metal alkoxides, alkaline earth metalhydroxides, alkali metal alkoxides or alkali metal hydroxides, such assodium methoxide, sodium ethoxide, potassium tert-butoxide, sodiumhydroxide, potassium hydroxide and calcium hydroxide).

7b) The hydrolysis of VIIId to VIIIc is normally carried out from 0° C.to 130° C., preferably 20° C. to 110° C., in an inert solvent in thepresence of an acid.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol and also dimethylsulfoxide and dimethylformamide, especially preferably dioxane. Mixturesof these may also be used.

Acids and acidic catalysts which are used are inorganic acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids, such as boron trifluoride, aluminumtrichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chlorideand zinc(II) chloride, especially preferably hydrochloric acid, and alsoorganic acids such as formic acid, acetic acid, propionic acid, oxalicacid, citric acid and trifluoroacetic acid. In general, the acids areemployed in catalytic amounts, but they can also be used in equimolaramounts, in an excess, or, if desired, as the solvent.

7c) The oximation of VIIIc to Vc is carried out in general and inparticular under the conditions described above under item 2b) for thepreparation of I from IVb.

When preparing compounds I according to the invention, it is generallyirrelevant whether the starting materials and intermediates containingthe phenyl or the benzyl moiety (formulae III, IV and X) and the ethersof the formula I already contain the group Q or whether this position isoccupied by a group which can be converted into Q by the processesdescribed in the literature cited at the outset. In principle the groupQ can be synthesized at any of the levels mentioned (formulae II, IV, Xand I).

In the novel intermediates of the general formula II, ##STR14## thesubstituents R², R³ and R⁴ and the index x have the meaning given at theoutset and L and Z are the following groups:

L is hydroxyl or a nucleophilically exchangeable leaving group;

Z is oxygen or a group NOR¹, R¹ having the meaning given at the outset.

In the novel intermediates of the general formula X ##STR15## thesubstituents Q, R², R³, R⁴ and R⁵ and the indices n, x and y have themeanings given at the outset and Y is one of the following groups:halogen or CO--R², R² having the meaning given at the outset.

The reaction mixtures are worked up in the customary manner, eg. bymixing with water, phase separation and, if desired chromatographicpurification of the crude products. In some cases, the intermediates andend products are obtained in the form of colorless or pale brown viscousoils, which are purified or freed from volatile components under reducedpressure and moderately elevated temperatures. If the intermediates andend products obtained are solids, they may also be purified byrecrystallization or digestion.

Due to their C═C-- and C═N-double bonds the compounds I can be obtainedfrom their preparation in the form of E/Z isomer mixtures, which can beseparated into the individual compounds in the customary manner, eg. bycrystallization or chromatography.

If isomer mixtures are obtained from the synthesis, however, aseparation is generally not absolutely necessary, since in some casesindividual isomers can be converted into each other during formulationfor use, or upon use (eg. when exposed to light, acids or bases).Similar conversions can also take place after application, for examplein the treatment of plants in the treated plant or in the harmful fungusor animal pest to be controlled.

With regard to their activity, the E isomers of the compounds I arepreferred as far as the C═NOR¹ double bond is concerned (configurationbased on the R² group relative to the OR¹ group).

In the definitions of the symbols mentioned in the above formulae,collective terms were used which generally represent the followingsubstituents:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: saturated, straight-chain or branched hydrocarbon radicals having1 to 4, 6, 8 or 10 carbon atoms, eg. C₁ -C₆ -alkyl, such as methyl,ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-di-methylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

Haloalkyl: straight-chain or branched alkyl groups having 1 to 10 carbonatoms (as mentioned above), it being possible for some or all of thehydrogen atoms in these groups to be replaced by halogen atoms asmentioned above, eg. C₁ --C₂ -haloalkyl, such as chloromethyl,bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkoxy: straight-chain or branched alkyl groups having 1 to 10 carbonatoms (as mentioned above) which are linked to the skeleton via anoxygen atom (--O--);

Haloalkoxy: straight-chain or branched haloalkyl groups having 1 to 10carbon atoms (as mentioned above) which are linked to the skeleton viaan oxygen atom (--O--);

Alkylthio: straight-chain or branched alkyl groups having 1 to 10 or 1to 4 carbon atoms (as mentioned above) which are linked to the skeletonvia a sulfur atom (--S--);

Alkylamino: a straight-chain or branched alkyl group having 1 to 10carbon atoms (as mentioned above) which is linked to the skeleton via anamino group (--NH--);

Dialkylamino: two straight-chain or branched alkyl groups, independentof one another, having in each case 1 to 10 carbon atoms (as mentionedabove) and being linked to the skeleton via a nitrogen atom;

Alkylcarbonyl: a straight-chain or branched alkyl group having 1 to 10carbon atoms (as mentioned above) which is linked to the skeleton via acarbonyl group (--CO--);

Alkoxycarbonyl: an alkoxy group having 1 to 10 carbon atoms (asmentioned above) which is linked to the skeleton via a carbonyl group(--CO--);

Alkylthiocarbonyl: an alkylthio group having 1 to 10 carbon atoms (asmentioned above) which is linked to the skeleton via a carbonyl group(--CO--);

Alkylaminocarbonyl: an alkylamino group having 1 to 10 carbon atoms (asmentioned above) which is linked to the skeleton via a carbonyl group(--CO--);

Dialkylaminocarbonyl: a dialkylamino group (as mentioned above), whichis linked to the skeleton via a carbonyl group (--CO--);

Alkylcarbonyloxy: a straight-chain or branched alkyl group having 1 to10 carbon atoms (as mentioned above) which is linked to the skeleton viaa carbonyloxy group (--CO₂ --);

Alkylcarbonylthio: a straight-chain or branched alkyl group having 1 to10 carbon atoms (as mentioned above) which is linked to the skeleton viaa carbonylthio group (--COS--);

Alkylcarbonylamino: a straight-chain or branched alkyl group having 1 to10 carbon atoms (as mentioned above) which is linked to the skeleton viaa carbonylamino group (--CONH--);

Alkylsulfonyl: a straight-chain or branched alkyl group having 1 to 10carbon atoms (as mentioned above) which is linked to the skeleton via asulfonyl group (--SO₂ --);

Alkoxysulfonyl: an alkoxy group having 1 to 10 carbon atoms (asmentioned above) which is linked to the skeleton via a sulfonyl group(--SO₂ --);

Alkylthiosulfonyl: an alkylthio group having 1 to 10 carbon atoms (asmentioned above) which is linked to the skeleton via a sulfonyl group(--SO₂ --);

Alkylaminosulfonyl: an alkylamino group having 1 to 10 carbon atoms (asmentioned above) which is linked to the skeleton via a sulfonyl group(--SO₂ --);

Dialkylaminosulfonyl: a dialkylamino group (as mentioned above) which islinked to the skeleton via a sulfonyl group (--SO₂ --);

Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicalshaving 2 to 4, 6, 8 or 10 carbon atoms and a double bond in anyposition, eg. C₂ -C₆ -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl,1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,2-methyl-l-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl,1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl,5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl,3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl,1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl,3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl,1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl,2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and1-ethyl-2-methyl-2-propenyl;

Haloalkenyl: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a double bond in any position(as mentioned above), it being possible for some or all of the hydrogenatoms in these groups to be replaced by halogen atoms as mentionedabove, in particular fluorine, chlorine and bromine;

Alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicalshaving 3 to 10 carbon atoms and a double bond in any position which isnot adjacent to the hetero atom (as mentioned above) which are linked tothe skeleton via an oxygen atom (--O--);

Haloalkenyloxy: unsaturated, straight-chain or branched alkenyloxygroups having 3 to 10 carbon atoms (as mentioned above), it beingpossible for some or all of the hydrogen atoms in these groups to bereplaced by halogen atoms as mentioned above, in particular fluorine,chlorine and bromine;

Alkenylthio: unsaturated, straight-chain or branched hydrocarbonradicals having 3 to 10 carbon atoms and a double bond in any positionwhich is not adjacent to the hetero atom (as mentioned above) which arelinked to the skeleton via a sulfur atom (--S--);

Alkenylamino: unsaturated, straight-chain or branched hydrocarbonradicals having 3 to 10 carbon atoms and a double bond in any positionwhich is not adjacent to the hetero atom (as mentioned above) which arelinked to the skeleton via an amino group (--NH--);

Alkenylcarbonyl: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a double bond in any position(as mentioned above) which are linked to the skeleton via a carbonylgroup (--CO--);

Alkenyloxycarbonyl: straight-chain or branched alkenyloxy groups having3 to 10 carbon atoms (as mentioned above) which are linked to theskeleton via a carbonyl group (--CO--);

Alkenylthiocarbonyl: straight-chain or branched alkenylthio groupshaving 3 to 10 carbon atoms (as mentioned above) which are linked to theskeleton via a carbonyl group (--CO--);

Alkenylaminocarbonyl: straight-chain or branched alkenylamino groupshaving 3 to 10 carbon atoms (as mentioned above) which are linked to theskeleton via a carbonyl group (--CO--);

Alkenylcarbonyloxy: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a double bond in any position(as mentioned above) which are linked to the skeleton via a carbonyloxygroup (--CO₂ --);

Alkenylcarbonylthio: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a double bond in any position(as mentioned above) which are linked to the skeleton via a carbonylthiogroup (--COS--);

Alkenylcarbonylamino: unsaturated, straight-chain or branchedhydrocarbon radicals having 2 to 10 carbon atoms and a double bond inany position (as mentioned above) which are linked to the skeleton via acarbonylamino group (--CONH--);

Alkenylsulfonyl: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a double bond in any position(as mentioned above) which are linked to the skeleton via asulfonylamino group (--SO₂ --);

Alkenyloxysulfonyl: a straight-chain or branched alkenyloxy group having3 to 10 carbon atoms (as mentioned above) which is linked to theskeleton via a sulfonyl group (--SO₂ --);

Alkenylthiosulfonyl: a straight-chain or branched alkenylthio grouphaving 3 to 10 carbon atoms (as mentioned above) which is linked to theskeleton via a sulfonyl group (--SO₂ --);

Alkenylaminosulfonyl: a straight-chain or branched alkenylamino grouphaving 3 to 10 carbon atoms (as mentioned above) which is linked to theskeleton via a sulfonyl group (--SO₂ --);

Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6,8 or 10 carbon atoms and a triple bond in any position, eg. C₂ -C₆-alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl,3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl,4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl,3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl,3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl- 1-methyl-2-propynyl;

Haloalkynyl: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a triple bond in any position(as mentioned above), it being possible for some or all of the hydrogenatoms in these groups to be replaced by halogen atoms as mentionedabove, in particular fluorine, chlorine and bromine;

Alkynyloxy: unsaturated, straight-chain or branched hydrocarbon radicalshaving 3 to 10 carbon atoms and a triple bond in any position which isnot adjacent to the hetero atom (as mentioned above) which are linked tothe skeleton via an oxygen atom (--O--);

Haloalkynyloxy: unsaturated, straight-chain or branched alkynyloxygroups having 3 to 10 carbon atoms (as mentioned above), it beingpossible for some or all of the hydrogen atoms in these groups to bereplaced by halogen atoms as mentioned above, in particular fluorine,chlorine and bromine;

Alkynylthio: unsaturated, straight-chain or branched hydrocarbonradicals having 3 to 10 carbon atoms and a triple bond in any positionwhich is not adjacent to the hetero atom (as mentioned above) which arelinked to the skeleton via a sulfur atom (--S--);

Alkynylamino: unsaturated, straight-chain or branched hydrocarbonradicals having 3 to 10 carbon atoms and a triple bond in any positionwhich is not adjacent to the hetero atom (as mentioned above) which arelinked to the skeleton via an amino group (--NH--);

Alkynylcarbonyl: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a triple bond in any position(as mentioned above) which are linked to the skeleton via a carbonylgroup (--CO--);

Alkynyloxycarbonyl: straight-chain or branched alkynyloxy groups having3 to 10 carbon atoms (as mentioned above) which are linked to theskeleton via a carbonyl group (--CO--);

Alkynylthiocarbonyl: straight-chain or branched alkynylthio groupshaving 3 to 10 carbon atoms (as mentioned above) which are linked to theskeleton via a carbonyl group (--CO--);

Alkynylaminocarbonyl: straight-chain or branched alkynylamino groupshaving 3 to 10 carbon atoms (as mentioned above) which are linked to theskeleton via a carbonyl group (--CO--);

Alkynylcarbonyloxy: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a triple bond in any position(as mentioned above) which are linked to the skeleton via a carbonyloxygroup (--CO₂ --);

Alkynylcarbonylthio: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a triple bond in any position(as mentioned above) which are linked to the skeleton via a carbonylthiogroup (--COS--);

Alkynylcarbonylamino: unsaturated, straight-chain or branchedhydrocarbon radicals having 2 to 10 carbon atoms and a triple bond inany position (as mentioned above) which are linked to the skeleton via acarbonylamino group (--CONH--);

Alkynylsulfonyl: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a triple bond in any position(as mentioned above) which are linked to the skeleton via a sulfonylgroup (--SO₂ --);

Alkynyloxysulfonyl: a straight-chain or branched alkynyloxy group having3 to 10 carbon atoms (as mentioned above) which is linked to theskeleton via a sulfonyl group (--SO₂ --);

Alkynylthiosulfonyl: a straight-chain or branched alkynylthio grouphaving 3 to 10 carbon atoms (as mentioned above) which is linked to theskeleton via a sulfonyl group (--SO₂ --);

Alkynylaminosulfonyl: a straight-chain or branched alkynylamino grouphaving 3 to 10 carbon atoms (as mentioned above) which is linked to theskeleton via a sulfonyl group(--SO₂ --);

Cycloalkyl: monocyclic, saturated hydrocarbon groups having 3 to 6, 8,10 or 12 carbon ring members, eg. C₃ -C₈ -cycloalkyl, such ascyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl;

Cycloalkoxy: monocyclic, saturated hydrocarbon groups having 3 to 12carbon ring members (as mentioned above) which are linked to theskeleton via an oxygen atom (--O--);

Cycloalkylthio: monocyclic, saturated hydrocarbon groups having 3 to 12carbon ring members (as mentioned above) which are linked to theskeleton via a sulfur atom (--S--);

Cycloalkylamino: monocyclic, saturated hydrocarbon groups having 3 to 12carbon ring members (as mentioned above) which are linked to theskeleton via an amino group (--NH--);

Cycloalkylcarbonyl: monocyclic, saturated hydrocarbon groups having 3 to12 carbon ring members (as mentioned above) which are linked to theskeleton via a carbonyl group (--CO--);

Cycloalkoxycarbonyl: a monocyclic cycloalkoxy group having 3 to 12carbon ring members (as mentioned above) which is linked to the skeletonvia a carbonyl group (--CO--);

Cycloalkylthiocarbonyl: a monocyclic cycloalkylthio group having 3 to 12carbon ring members (as mentioned above) which is linked to the skeletonvia a carbonyl group (--CO--);

Cycloalkylaminocarbonyl: a monocyclic cycloalkylamino group having 3 to12 carbon ring members (as mentioned above) which is linked to theskeleton via a carbonyl group (--CO--);

Cycloalkylcarbonyloxy: monocyclic, saturated hydrocarbon groups having 3to 12 carbon ring members (as mentioned above) which are linked to theskeleton via a carbonyloxy group (--CO₂ --);

Cycloalkylcarbonylthio: monocyclic, saturated hydrocarbon groups having3 to 12 carbon ring members (as mentioned above) which are linked to theskeleton via a carbonylthio group (--COS--);

Cycloalkylcarbonylamino: monocyclic, saturated hydrocarbon groups having3 to 12 carbon ring members (as mentioned above) which are linked to theskeleton via a carbonylamino group (--CONH--);

Cycloalkylsulfonyl: monocyclic, saturated hydrocarbon groups having 3 to12 carbon ring members (as mentioned above) which are linked to theskeleton via a sulfonyl group (--SO₂ --);

Cycloalkoxysulfonyl: a monocyclic cycloalkoxy group having 3 to 12carbon ring members (as mentioned above) which is linked to the skeletonvia a sulfonyl group (--SO₂ --);

Cycloalkylthiosulfonyl: a monocyclic cycloalkylthio group having 3 to 12carbon ring members (as mentioned above) which is linked to the skeletonvia a sulfonyl group (--SO₂ --);

Cycloalkylaminosulfonyl: a monocyclic cycloalkylamino group having 3 to12 carbon ring members (as mentioned above) which is linked to theskeleton via a sulfonyl group (--SO₂ --);

saturated or partially unsaturated cyclic radical, which, besides carbonatoms, can contain, as ring members, hetero atoms from the groupconsisting of oxygen, sulfur or nitrogen: cycloalkyl having 3 to 12carbon ring members as mentioned above or 5- or 6-membered heterocycles(heterocyclyl) containing, besides carbon ring members, one to threenitrogen atoms and/or an oxygen or sulfur atom or one or two oxygenand/or sulfur atoms, eg. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl,2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl,3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2,3-pyrrolin-2-yl, 2,3-pyrrolin-3-yl,2,4-pyrrolin-2-yl, 2,4-pyrrolin-3-yl, 2,3-isoxazolin-3-yl,3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl,3,4-isoxazolin-4-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl,3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl,3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl,3,4-isothiazolin-4-yl, 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl,3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl,2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl,2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl,3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl,4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl,4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl,3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl,4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazinyl,4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl,4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydro-triazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl;

Heterocyclyloxy: a 5- or 6-membered heterocycle (as mentioned above)which is linked to the skeleton via an oxygen atom (--O--);

Heterocyclylthio: a 5- or 6-membered heterocycle (as mentioned above)which is linked to the skeleton via a sulfur atom (--S--);

Heterocyclylamino: a 5- or 6-membered heterocycle (as mentioned above)which is linked to the skeleton via an amino group (--NH--);

Heterocyclylcarbonyl: a 5- or 6-membered heterocycle (as mentionedabove) which is linked to the skeleton via a carbonyl group (--CO--);

Heterocyclyloxycarbonyl: a heterocyclyloxy group (as mentioned above)which is linked to the skeleton via a carbonyl group (--CO--);

Heterocyclylthiocarbonyl: a heterocyclylthio group (as mentioned above)which is linked to the skeleton via a carbonyl group (--CO--);

Heterocyclylaminocarbonyl: a 5- or 6-membered heterocycle (as mentionedabove) which is linked to the skeleton via an aminocarbonyl group(--NHCO--);

Heterocyclylcarbonyloxy: a 5- or 6-membered heterocycle (as mentionedabove) which is linked to the skeleton via a carbonyloxy group (--CO₂--);

Heterocyclylcarbonylthio: a 5- or 6-membered heterocycle (as mentionedabove) which is linked to the skeleton via a carbonylthio group(--COS--);

Heterocyclylcarbonylamino: a 5- or 6-membered heterocycle (as mentionedabove) which is linked to the skeleton via a carbonylamino group(--CONH--);

Heterocyclylsulfonyl: a 5- or 6-membered heterocycle (as mentionedabove) which is linked to the skeleton via a sulfonyl group (--SO₂ --);

Aryloxysulfonyl: a heterocyclyloxy group (as mentioned above) which islinked to the skeleton via a sulfonyl group (--SO₂ --);

Heterocyclylthiosulfonyl: a heterocyclylthio group (as mentioned above)which is linked to the skeleton via a sulfonyl group (--SO₂ --);

Heterocyclylaminosulfonyl: a heterocyclylamino group (as mentionedabove) which is linked to the skeleton via a sulfonyl group (--SO₂ --);

Aryl: a mono- to trinuclear aromatic ring system containing 6 to 14carbon ring members, eg. phenyl, naphthyl and anthracenyl;

Aryloxy: a mono- to trinuclear aromatic ring system (as mentioned above)which is linked to the skeleton via an oxygen atom (--O--);

Arylthio: a mono- to trinuclear aromatic ring system (as mentionedabove) which is linked to the skeleton via a sulphur atom (--S--);

Arylamino: a mono- to trinuclear aromatic ring system (as mentionedabove) which is linked to the skeleton via an amino group (--NH--);

Arylcarbonyl: a mono- to trinuclear aromatic ring system (as mentionedabove) which is linked to the skeleton via a carbonyl group (--CO--);

Aryloxycarbonyl: a mono- to trinuclear aryloxy group (as mentionedabove) which is linked to the skeleton via a carbonyl group (--CO--);

Arylthiocarbonyl: a mono- to trinuclear arylthio group (as mentionedabove) which is linked to the skeleton via a carbonyl group (--CO--);

Arylaminocarbonyl: a mono- to trinuclear arylamino group (as mentionedabove) which is linked to the skeleton via a carbonyl group (--CO--);

Arylcarbonyloxy: a mono- to trinuclear aromatic ring system (asmentioned above) which is linked to the skeleton via a carbonyloxy group(--CO₂ --);

Arylcarbonylthio: a mono- to trinuclear aromatic ring system (asmentioned above) which is linked to the skeleton via a carbonylthiogroup (--COS--);

Arylcarbonylamino: a mono- to trinuclear aromatic ring system (asmentioned above) which is linked to the skeleton via a carbonylaminogroup (--CONH--);

Arylsulfonyl: a mono- to trinuclear aromatic ring system (as mentionedabove) which is linked to the skeleton via a sulfonyl group (--SO₂ --);

Aryloxysulfonyl: a mono- to trinuclear aryloxy group (as mentionedabove) which is linked to the skeleton via a sulfonyl group (--SO₂ --);

Arylthiosulfonyl: a mono- to trinuclear arylthio group (as mentionedabove) which is linked to the skeleton via a sulfonyl group (--SO₂ --);

Arylaminosulfonyl: a mono- to trinuclear arylamino group (as mentionedabove) which is linked to the skeleton via a sulfonyl group (--SO₂ --);

aromatic ring system, which, besides carbon ring members, can containhetero atoms from the group consisting of oxygen, sulfur and nitrogen:aryl as mentioned above or mono- or binuclear hetaryl, eg.

5-membered hetaryl, containing one to four nitrogen atoms or one tothree nitrogen atoms and a sulfur or oxygen atom: 5-membered hetarylring groups, which, besides carbon atoms, may contain, as ring members,one to four nitrogen atoms or one to three nitrogen atoms and a sulfuror oxygen atom, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl,3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and1,3,4-triazol-2-yl;

benzo-fused 5-membered hetaryl, containing one to three nitrogen atomsor a nitrogen atom and an oxvgen of sulfur atom: 5-membered hetaryl ringgroups, which, besides carbon atoms, may contain, as ring members, oneto four nitrogen atoms or one to three nitrogen atoms and a sulfur oroxygen atom and in which two adjacent carbon ring members or a nitrogenand an adjacent carbon ring members can be bridged by a buta-1,3-diene-1,4-diyl group;

5-membered hetarvl, linked via nitrogen and containing one to fournitrogen atoms, or benzo-fused 5-membered hetaryl, linked via nitrogenand containing one to three nitrogen atoms: 5-membered hetaryl ringgroups which, besides carbon atoms, may contain, as ring members, one tofour nitrogen atoms, or one to three nitrogen atoms, and in which twoadjacent carbon ring members or a nitrogen and an adjacent carbon ringmember can be bridged by a buta-1,3-diene-1,4-diyl group, these ringsbeing linked to the skeleton via one of the nitrogen ring members;

6-membered hetaryl, containing one to three, or one to four, nitrogenatoms: 6-membered hetaryl ring groups which, besides carbon atoms, maycontain, as ring members, one to three, or one to four, nitrogen atoms,eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;

Hetaryloxy: a mono- to trinuclear heteroaromatic ring system (asmentioned above) which is linked to the skeleton via an oxygen atom(--O--);

Hetarylthio: a mono- to trinuclear heteroaromatic ring system (asmentioned above) which is linked to the skeleton via a sulfur atom(--S--);

Hetarylamino: a mono- to trinuclear heteroaromatic ring system (asmentioned above) which is linked to the skeleton via an amino group(--NH--);

Hetarylcarbonyl: a mono- to trinuclear heteroaromatic ring system (asmentioned above) which is linked to the skeleton via a carbonyl group(--CO--);

Hetaryloxycarbonyl: a mono- to trinuclear hetaryloxy group (as mentionedabove) which is linked to the skeleton via a carbonyl group (--CO--);

Hetarylthiocarbonyl: a mono- to trinuclear hetarylthio group (asmentioned above) which is linked to the skeleton via a carbonyl group(--CO--);

Hetarylaminocarbonyl: a mono- to trinuclear hetarylamino group (asmentioned above) which is linked to the skeleton via a carbonyl group(--CO--);

Hetarylcarbonyloxy: a mono- to trinuclear heteroaromatic ring system (asmentioned above) which is linked to the skeleton via a carbonyloxy group(--CO₂ --);

Hetarylcarbonylthio: a mono- to trinuclear heteroaromatic ring system(as mentioned above) which is linked to the skeleton via a carbonylthiogroup (--COS--);

Hetarylcarbonylamino: a mono- to trinuclear heteroaromatic ring system(as mentioned above) which is linked to the skeleton via carbonylaminogroup (--CONH--);

Hetarylsulfonyl: a mono- to trinuclear heteroaromatic ring system (asmentioned above) which is linked to the skeleton via a sulfonyl group(--SO₂ --);

Hetaryloxysulfonyl: a mono- to trinuclear hetaryloxy group (as mentionedabove) which is linked to the skeleton via a sulfonyl group (--SO₂ --);

Hetarylthiosulfonyl: a mono- to trinuclear hetarylthio group (asmentioned above) which is linked to the skeleton via a sulfonyl group(--SO₂ --);

Hetarylaminosulfonyl: a mono- to trinuclear hetarylamino group (asmentioned above) which is linked to the skeleton via a sulfonyl group(--SO₂ --);

Alkylene: divalent unbranched chains of 3 to 5 CH₂ groups, eg. CH₂, CH₂CH₂, CH₂ CH₂ CH₂, CH₂ CH₂ CH₂ CH₂ and CH₂ CH₂ CH₂ CH₂ CH₂ ;

Oxyalkylene: divalent unbranched chains of 2 to 4 CH₂ groups, onevalency being linked to the skeleton via an oxygen atom, eg. OCH₂ CH₂,OCH₂ CH₂ CH₂ and OCH₂ CH₂ CH₂ CH₂ ;

Oxyalkyleneoxy: divalent unbranched chains of 1 to 3 CH₂ groups, bothvalencies being linked to the skeleton via an oxygen atom, eg. OCH₂ O,OCH₂ CH₂ O and OCH₂ CH₂ CH₂ O;

Alkenylene: divalent unbranched chains of 1 to 3 CH₂ groups and oneCH═CH group in any position, eg. CH═CHCH₂, CH₂ CH═CHCH₂, CH═CHCH₂ CH₂,CH₂ CH═CHCH₂ CH₂ and CH═CHCH₂ CH₂ CH₂ ;

Oxyalkenylene: divalent unbranched chains of 0 to 2 CH₂ groups and oneCH═CH group in any position, one valency being linked to the skeletonvia an oxygen atom, eg. OCH═CH, OCH═CHCH₂, OCH₂ CH═CH, OCH₂ CH═CHCH₂,OCH═CHCH₂ CH₂ and OCH₂ CH₂ --CH═CH;

Oxyalkenyleneoxy: divalent unbranched chains of 0 to 2 CH₂ groups andone CH═CH group in any position, both valencies being linked to theskeleton via an oxygen atom, eg. OCH═CHO, OCH═CHCH₂ O, OCH₂ CH═CHCH₂ Oand OCH═CHCH₂ CH₂ O;

organic radical: unsubstituted or substituted alkyl, alkenyl, alkynyl,cycloalkyl, heterocyclyl, aryl or hetaryl.

The term "unsubstituted or substituted" relating to alkyl, alkenyl andalkynyl groups is intended to express that these groups may be partiallyor fully halogenated [ie. some or all of the hydrogen atoms in thesegroups may be replaced by identical or different halogen atoms asmentioned above (preferably fluorine, chlorine or bromine)] and/or canhave attached to them one to three (preferably one) of the followingradicals:

cyano, nitro, hydroxyl, amino, formyl, carboxyl, aminocarbonyl, alkoxy,haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino,alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl,dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino,alkylcarbonyl-N-alkylamino and alkylcarbonyl-N-alkylamino, the alkylgroups in these radicals preferably containing 1 to 6 carbon atoms, inparticular 1 to 4 carbon atoms;

cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino,cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino,unsubstituted or substituted by customary groups, the cyclic systemscontaining 3 to 12 ring members, preferably 2 to 8 ring members, inparticular 3 to 6 ring members and the alkyl groups in these radicalspreferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbonatoms;

aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy,arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl,hetaryloxy, hetarylthio, hetarylamino, hetaryl-N-alkylamino,hetarylalkoxy, hetarylalkylthio, hetarylalkylamino and hetarylalkyl-N-alkylamino, unsubstituted or substituted by customary groups, the arylradicals preferably containing 6 to 10 ring members, in particular 6ring members (phenyl), the hetaryl radicals containing, in particular, 5or 6 ring members and the alkyl groups in these radicals preferablycontaining 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms.

The term "ubsubstituted or substituted" when relating to the cyclic(saturated, unsaturated or aromatic) groups is intended to express thatthese groups may be partially or fully halogenated [ie. some or all ofthe hydrogen atoms in these groups may be replaced by identical ordifferent halogen atoms as mentioned above (preferably fluorine,chlorine or bromine, in particular fluorine or chlorine)] and/or canhave attached to them one to four (in particular one to three) of thefollowing radicals:

cyano, nitro, hydroxyl, amino, carboxyl, aminocarbonyl, alkyl,haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl,haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy, haloalkoxy, alkylthio,haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl,alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl,alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-N-alkylamino andalkylcarbonyl-N-alkylamino, the alkyl groups in these radicalspreferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbonatoms, and the alkenyl or alkynyl groups mentioned in these radicalscontaining 2 to 8, preferably 2 to 6, in particular 2 to 4, carbonatoms;

and/or one to three (in particular one) of the following radicals:

cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino,cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino,unsubstituted or substituted by customary groups, the cyclic systemscontaining 3 to 12 ring members, preferably 2 to 8 ring members, inparticular 3 to 6 ring members and the alkyl groups in these radicalspreferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbonatoms;

aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylalkoxy,arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl,hetaryloxy, hetarylthio, hetarylamino, hetaryl-N-alkylamino,hetarylalkoxy, hetarylalkylthio, hetarylalkylamino andhetarylalkyl-N-alkylamino, unsubstituted or substituted by customarygroups, the aryl radicals preferably containing 6 to 10 ring members, inparticular 6 ring members (phenyl), the hetaryl radicals containing inparticular 5 or 6 ring members and the alkyl groups in these radicalspreferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbonatoms;

and/or one or two (in particular one) of the following radicals:

formyl,

CR^(iii) ═NOR^(iv) [where R^(iii) is hydrogen, alkyl, cycloalkyl andaryl and R^(iv) is alkyl, alkenyl, haloalkenyl, alkynyl and arylalkyl(the abovementioned alkyl groups preferably containing 1 to 6 carbonatoms, in particular 1 to 4 carbon atoms, the abovementioned cycloalkylgroups, alkenyl groups and alkynyl groups preferably containing 3 to 8,in particular 3 to 6, carbon atoms) and aryl is in particular phenylwhich is unsubstituted or can be substituted by customary groups] or

NR^(v) --CO--D--R^(vi) [where R^(v) is hydrogen, hydroxyl, C₁ -C₆-alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₂ -C₆-alkenyloxy, C₂ -C₆ -alkynyloxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkoxy and C₁ -C₆ -alkoxycarbonyl, R^(vi) is hydrogen,C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₃-C₆ -cycloalkenyl, aryl, aryl-C₁ -C₆ -alkyl, hetaryl and hetaryl-C₁ -C₆-alkyl and D is a direct linkage, oxygen or nitrogen, it being possiblefor the nitrogen to have attached to it one of the groups mentionedunder R^(vi) ],

and/or where two adjacent C atoms of the cyclic systems can haveattached to them a C₃ -C₅ -alkylene, C₃ -C₅ -alkenylene, oxy-C₂ -C₄-alkylene, oxy-C₁ -C₃ -alkyleneoxy, oxy-C₂ -C₄ -alkenylene, oxy-C₂ -C₄-alkenyleneoxy or butadienediyl group, it being possible for thesebridges, in turn, to be partially or fully halogenated and/or to haveattached to them one to three, in particular one or two of the followingradicals:

C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy andC₁ -C₄ -alkylthio.

Customary groups are to be understood as meaning in particular thefollowing substituents: halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄-haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylamino,di-C₁ -C₄ -alkylamino and C₁ -C₄ -alkylthio.

Especially preferred compounds I are those where Q is C(CO₂ CH₃)═CHCH₃,C(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃ or N(OCH₃)--CO₂CH₃.

Other especially preferred compounds of the formula I are those where R¹is hydrogen or one of the following groups: unsubstituted or substitutedalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or hetaryl.

Moreover, especially preferred compounds I are those where R¹ isunsubstituted or substituted C₁ -C₆ -alkyl.

Equally, especially preferred compounds I are those where R¹ isunsubstituted or substituted C₃ -C₆ -alkenyl.

Besides, especially preferred compounds I are those where R¹ isunsubstituted or substituted C₃ -C₆ -alkynyl.

Other particularly preferred compounds I are those where R¹ is C₁ -C₆-haloalkyl.

Moreover, especially preferred compounds I are those where R¹ is C₃ -C₆-haloalkenyl.

Equally, especially preferred compounds I are those where R¹ is aryl-C₁-C₂ -alkyl, it being possible for the aryl radical to be unsubstitutedor substituted.

Especially preferred compounds I are those where R¹ is aryl-C₁ -C₂-alkyl, it being possible for the aryl radical to be partially or fullyhalogenated and/or to have attached to it one to three of the followinggroups: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄ -alkoxy.

Besides, especially preferred compounds I are those where R¹ is C₃ -C₆-cycloalkyl-C₁ -C₂ -alkyl, it being possible for the cycloalkyl radicalto be unsubstituted or substituted.

Especially preferred compounds I are those where R¹ is C₃ -C₆-cycloalkyl-C₁ -C₂ -alkyl, it being possible for the cycloalkyl radicalto be partially or fully halogenated and/or to have attached to it oneto three C₁ -C₄ -alkyl groups.

Furthermore, especially preferred compounds I are those where R¹ ishetaryl-C₁ -C₂ -alkyl, it being possible for the hetaryl radical to beunsubstituted or substituted.

Especially preferred compounds I are those where R¹ is hetaryl-C₁ -C₂-alkyl, it being possible for the hetaryl radical to be partially orfully halogenated and/or to have attached to it one to three of thefollowing groups: C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄ -alkoxy.

Moreover, especially preferred compounds of the formula I are thosewhere R² is hydrogen or one of the following groups: unsubstituted orsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl orhetaryl, it being possible for these groups to be linked to the skeletondirectly (by a carbon atom) or by an oxygen, sulfur or nitrogen atom.

Particularly preferred compounds I are those where R² is unsubstitutedor substituted C₁ -C₆ -alkyl.

Moreover, especially preferred compounds I are those where R² isunsubstituted or substituted C₂ -C₆ -alkenyl.

Equally, especially preferred compounds I are those where R² isunsubstituted or substituted C₂ -C₆ -alkynyl.

Besides, especially preferred compounds I are those where R² is C₃ -C₆-cycloalkyl.

Other particularly preferred compounds I are those where R² is aryl.

Moreover, especially preferred compounds I are those where R² ishetaryl.

Moreover, especially preferred compounds I are those where R³ ishydrogen, halogen, C₁ -C₃ -alkyl or C₁ -C₂ -haloalkyl, in particularhydrogen, methyl, fluorine, chlorine, ethyl, isopropyl andtrifluoromethyl.

Particularly preferred compounds I are those where R³ is hydrogen.

Furthermore, especially preferred compounds I are those where R³ ishalogen, in particular fluorine, chlorine and bromine.

Equally, especially preferred compounds I are those where R³ is methyl.

Besides, especially preferred compounds I are those where R³ is C₁-haloalkyl, in particular trifluoromethyl.

Furthermore, preferred compounds I are those where R⁴ is hydrogen.

Besides, preferred compounds I are those where R⁴ is halogen, inparticular fluorine, chlorine and bromine.

Moreover, especially preferred compounds I are those where R⁴ is C₁ -C₂-alkyl.

Equally, especially preferred compounds I are those where R⁴ is C₁ -C₂-alkoxy.

Besides, especially preferred compounds I are those where R⁴ is cyano.

Other particularly preferred compounds I are those where R⁴ is nitro.

Furthermore, especially preferred compounds I are those where y is 0, 1,2 or 3, it being possible for the radicals R⁵ to be different if y is 2or 3.

Especially preferred compounds I are those where y is 0 or 1.

Moreover, especially preferred compounds I are those where R⁵ is cyano,halogen, C₁ -C₃ -alkyl, C₁ -C₂ -halogenalkyl or C₁ -C₃ -alkoxy, inparticular cyano, fluorine, chlorine, methyl, ethyl, isopropyl,trifluoromethyl, methoxy or ethoxy.

Particularly preferred compounds I are those where R⁵ is methyl.

Moreover, especially preferred compounds I are those where R⁵ ismethoxy.

Equally, especially preferred compounds I are those where R⁵ isfluorine.

Besides, especially preferred compounds I where R⁵ is chlorine.

Other compounds I which are particularly preferred are those where R⁵ istrifluoromethyl.

Moreover, especially preferred compounds I are those where R⁵ is OCH₂ O.

Particularly preferred with a view to their use are the compounds Icompiled in the tables below. Moreover the groups mentioned in thetables for one substituent are, considered on their own, an especiallypreferred embodiment of the substituent in question, independently ofthe combination in which they are mentioned.

Table 1

Componds of the general formula IA.1 where R² is methyl, R³ is hydrogen,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A. ##STR16##

Table 2

Componds of the general formula IA.2 where R² is methyl, R³ is hydrogen,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A. ##STR17##

Table 3

Componds of the general formula IA.3, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR18##

Table 4

Componds of the general formula IA.4, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR19##

Table 5

Componds of the general formula IA.5, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR20##

Table 6

Componds of the general formula IA.6, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR21##

Table 7

Componds of the general formula IA.7, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR22##

Table 8

Componds of the general formula IA.8, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR23##

Table 9

Componds of the general formula IA.9, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR24##

Table 10

Componds of the general formula IA.10, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR25##

Table 11

Componds of the general formula IB.1, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR26##

Table 12

Componds of the general formula IB.2, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR27##

Table 13

Componds of the general formula IB.3, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR28##

Table 14

Componds of the general formula IB.4, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR29##

Table 15

Componds of the general formula IB.5, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR30##

Table 16

Componds of the general formula IB.6, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR31##

Table 17

Componds of the general formula IB.7, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR32##

Table 18

Componds of the general formula IB.8, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR33##

Table 19

Componds of the general formula IB.9, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR34##

Table 20

Componds of the general formula IB.10, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A. ##STR35##

Table 21

Componds of the general formula IA.1, where R² is methyl, R³ ishydrogen, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 22

Compounds of the general formula IA.2, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 23

Compounds of the general formula IA.3, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 24

Compounds of the general formula IA.4, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 25

Compounds of the general formula IA.5, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 26

Compounds of the general formula IA.6, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 27

Compounds of the general formula IA.7, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 28

Compounds of the general formula IA.8, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 29

Compounds of the general formula IA.9, where R² is methyl, R³ is methyl,R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compound correspondsto a group of Table A.

Table 30

Compounds of the general formula IA.10, where R² is methyl, R³ ismethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 31

Compounds of the general formula IA.1, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen, R¹ for each compoundcorresponds to a group of Table A.

Table 32

Compounds of the general formula IA.2, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 33

Compounds of the general formula IA.3, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 34

Compounds of the general formula IA.4, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 35

Compounds of the general formula IA.5, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 36

Compounds of the general formula IA.6, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 37

Compounds of the general formula IA.7, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 38

Compounds of the general formula IA.8, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 39

Compounds of the general formula IA.9, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 40

Compounds of the general formula IA.10, where R² is methyl, R³ ischlorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 41

Compounds of the general formula IA.1, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 42

Compounds of the general formula IA.2, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 43

Compounds of the general formula IA.3, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 44

Compounds of the general formula IA.4, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 45

Compounds of the general formula IA.5, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 46

Compounds of the general formula IA.6, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 47

Compounds of the general formula IA.7, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 48

Compounds of the general formula IA.8, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 49

Compounds of the general formula IA.9, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 50

Compounds of the general formula IA.10, where R² is methyl, R³ isfluorine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 51

Compounds of the general formula IA.1, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 52

Compounds of the general formula IA.2, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and RI for each compoundcorresponds to a group of Table A.

Table 53

Compounds of the general formula IA.3, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 54

Compounds of the general formula IA.4, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 55

Compounds of the general formula IA.5, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 56

Compounds of the general formula IA.6, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 57

Compounds of the general formula IA.7, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 58

Compounds of the general formula IA.8, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 59

Compounds of the general formula IA.9, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 60

Compounds of the general formula IA.10, where R² is methyl, R³ isbromine, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for each compoundcorresponds to a group of Table A.

Table 61

Compounds of the general formula IA.1, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 62

Compounds of the general formula IA.2, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 63

Compounds of the general formula IA.3, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 64

Compounds of the general formula IA.4, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 65

Compounds of the general formula IA.5, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 66

Compounds of the general formula IA.6, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 67

Compounds of the general formula IA.7, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 68

Compounds of the general formula IA.8, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 69

Compounds of the general formula IA.9, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

Table 70

Compounds of the general formula IA.10, where R² is methyl, R³ istrifluoromethyl, R⁴ is hydrogen, R⁵ _(y) is hydrogen and R¹ for eachcompound corresponds to a group of Table A.

                  TABLE A                                                         ______________________________________                                        No.       R.sup.1                                                             ______________________________________                                        A.1       H                                                                   A.2       CH.sub.3                                                            A.3       C.sub.2 H.sub.5                                                     A.4       n-C.sub.3 H.sub.7                                                   A.5       i-C.sub.3 H.sub.7                                                   A.6       cyclopropyl                                                         A.7       n-C.sub.4 H.sub.9                                                   A.8       s-C.sub.4 H.sub.9                                                   A.9       i-C.sub.4 H.sub.9                                                   A.10      t-C.sub.4 H.sub.9                                                   A.11      n-C.sub.5 H.sub.11                                                  A.12      i-C.sub.5 H.sub.11                                                  A.13      neo-C.sub.5 H.sub.11                                                A.14      cyclopentyl                                                         A.15      n-C.sub.6 H.sub.13                                                  A.16      cyclohexyl                                                          A.17      n-C.sub.8 H.sub.17                                                  A.18      CH.sub.2 CH.sub.2 Cl                                                A.19      (CH.sub.2).sub.4 Cl                                                 A.20      CH.sub.2 CN                                                         A.21      CH.sub.2 CH.sub.2 CN                                                A.22      (CH.sub.2).sub.3 CN                                                 A.23      (CH.sub.2).sub.4 CN                                                 A.24      (CH.sub.2).sub.6 CN                                                 A.25      cyclohexylmethyl                                                    A.26      2-cyclohexyleth-1-yl                                                A.27      cyclopropylmethyl                                                   A.28      2-cyclopropyleth-1-yl                                               A.29      2-methoxyeth-1-yl                                                   A.30      2-ethoxyeth-1-yl                                                    A.31      2-isopropoxyeth-1-yl                                                A.32      3-methoxyprop-1-yl                                                  A.33      3-ethoxyprop-1-yl                                                   A.34      3-isopropoxyprop-1-yl                                               A.35      4-methoxybut-1-yl                                                   A.36      4-isopropoxybut-1-yl                                                A.37      propen-3-yl                                                         A.38      but-2-en-1-yl                                                       A.39      3-methylbut-2-en-1-yl                                               A.40      2-vinyloxyeth-1-yl                                                  A.41      allyloxyeth-1-yl                                                    A.42      2-trifluoromethoxyeth-1-yl                                          A.43      3-trifluoromethoxyprop-1-yl                                         A.44      4-difluoromethoxybut-1-yl                                           A.45      hydroxycarbonylmethyl                                               A.46      methoxycarbonylmethyl                                               A.47      aminocarbonylmethyl                                                 A.48      N-methylaminocarbonylmethyl                                         A.49      N,N-dimethylaminocarbonyl-methyl                                    A.50      2-hydroxycarbonyleth-1-yl                                           A.51      2-methoxycarbonyleth-1-yl                                           A.52      2-aminocarbonyleth-1-yl                                             A.53      2-N-methylaminocarbonyleth-1-yl                                     A.54      2-dimethylaminocarbonyleth-1-yl                                     A.55      2-aminoeth-1-yl                                                     A.56      2-aminoprop-1-yl                                                    A.57      4-aminobut-1-yl                                                     A.58      3-dimethylaminoprop-1-yl                                            A.59      4-aminothiocarbonylbut-1-yl                                         A.60      2-oxopropyl                                                         A.61      cyclohexyl                                                          A.62      cyclopropyl                                                         A.63      cyclopentyl                                                         A.64      2-methoxyiminoprop-1-yl                                             A.65      2-methoxyiminoeth-1-yl                                              A.66      6-aminocarbonylhex-1-yl                                             A.67      3-aminothiocarbonylprop-1-yl                                        A.68      2-aminothiocarbonyleth-1-yl                                         A.69      aminothiocarbonylmethyl                                             A.70      4-(N,N-dimethylamino)but-1-yl                                       A.71      2-(methylthio)eth-1-yl                                              A.72      2-(methylsulfonyl)eth-1-yl                                          A.73      4-(methylthio)prop-1-yl                                             A.74      4-(methylsulfonyl)prop-1-yl                                         A.75      benzyl                                                              A.76      2-F--C.sub.6 H.sub.4 --CH.sub.2                                     A.77      3-F--C.sub.6 H.sub.4 --CH.sub.2                                     A.78      4-F--C.sub.6 H.sub.4 --CH.sub.2                                     A.79      2,3-F.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                            A.80      2,4-F.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                            A.81      2,5-F.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                            A.82      2,6-F.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                            A.83      3,4-F.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                            A.84      3,5-F.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                            A.85      2-Cl--C.sub.6 H.sub.4 --CH.sub.2                                    A.86      3-Cl--C.sub.6 H.sub.4 --CH.sub.2                                    A.87      4-Cl--C.sub.6 H.sub.4 --CH.sub.2                                    A.88      2,3-Cl.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.89      2,4-Cl.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.90      2,5-Cl.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.91      2,6-Cl.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.92      3,4-Cl.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.93      3,5-Cl.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.94      2,3,4-Cl.sub.3 --C.sub.6 H.sub.2 --CH.sub.2                         A.95      2,3,5-Cl.sub.3 --C.sub.6 H.sub.2 --CH.sub.2                         A.96      2,3,6-Cl.sub.3 --C.sub.6 H.sub.2 --CH.sub.2                         A.97      2,4,5-Cl.sub.3 --C.sub.6 H.sub.2 --CH.sub.2                         A.98      2,4,6-Cl.sub.3 --C.sub.6 H.sub.2 --CH.sub.2                         A.99      3,4,5-Cl.sub.3 --C.sub.6 H.sub.2 --CH.sub.2                         A.100     2-Br--C.sub.6 H.sub.4 --CH.sub.2                                    A.101     3-Br--C.sub.6 H.sub.4 --CH.sub.2                                    A.102     4-Br--C.sub.6 H.sub.4 --CH.sub.2                                    A.103     2,3-Br.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.104     2,4-Br.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.105     2,5-Br.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.106     2,6-Br.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.107     3,4-Br.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.108     3,5-Br.sub.2 --C.sub.6 H.sub.3 --CH.sub.2                           A.109     2-F, 3-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.110     2-F, 4-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.111     2-F, 5-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.112     2-F, 3-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.113     2-F, 4-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.114     2-F, 5-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.115     2-Cl, 3-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.116     2-Cl, 4-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.117     2-Cl, 5-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.118     3-F, 4-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.119     3-F, 5-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.120     3-F, 6-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.121     3-F, 4-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.122     3-F, 5-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.123     3-F, 6-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.124     3-Cl, 4-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.125     3-Cl, 5-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.126     3-Cl, 6-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.127     4-F, 5-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.128     4-F, 6-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.129     4-F, 5-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.130     4-F, 6-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.131     4-Cl, 5-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.132     5-F, 6-Cl--C.sub.6 H.sub.3 --CH.sub.2                               A.133     5-F, 6-Br--C.sub.6 H.sub.3 --CH.sub.2                               A.134     5-Cl, 6-Br--C.sub.6 H.sub.3 --CH.sub.2                              A.135     3-Br, 4-Cl, 5-Br--C.sub.6 H.sub.2 --CH.sub.2                        A.136     2-CN--C.sub.6 H.sub.4 --CH.sub.2                                    A.137     3-CN--C.sub.6 H.sub.4 --CH.sub.2                                    A.138     4-CN--C.sub.6 H.sub.4 --CH.sub.2                                    A.139     2-NO.sub.2 --C.sub.6 H.sub.4 --CH.sub.2                             A.140     3-NO.sub.2 --C.sub.6 H.sub.4 --CH.sub.2                             A.141     4-NO.sub.2 --C.sub.6 H.sub.4 --CH.sub.2                             A.142     2-CH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                             A.143     3-CH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                             A.144     4-CH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                             A.145     2,3-(CH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                   A.146     2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                   A.147     2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                   A.148     2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                   A.149     3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                   A.150     3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                   A.151     2-C.sub.2 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                      A.152     3-C.sub.2 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                      A.153     4-C.sub.2 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                      A.154     2-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4 --CH.sub.2                    A.155     3-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4 --CH.sub.2                    A.156     4-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4 --CH.sub.2                    A.157     2-cyclohexyl-C.sub.6 H.sub.4 --CH.sub.2                             A.158     3-cyclohexyl-C.sub.6 H.sub.4 --CH.sub.2                             A.159     4-cyclohexyl-C.sub.6 H.sub.4 --CH.sub.2                             A.160     2-vinyl-C.sub.6 H.sub.4 --CH.sub.2                                  A.161     3-vinyl-C.sub.6 H.sub.4 --CH.sub.2                                  A.162     4-vinyl-C.sub.6 H.sub.4 --CH.sub.2                                  A.163     2-allyl-C.sub.6 H.sub.4 --CH.sub.2                                  A.164     3-allyl-C.sub.6 H.sub.4 --CH.sub.2                                  A.165     4-allyl-C.sub.6 H.sub.4 --CH.sub.2                                  A.166     2-C.sub.6 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                      A.167     3-C.sub.6 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                      A.168     4-C.sub.6 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                      A.169     3-CH.sub.3, 5-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.3 --CH.sub.2        A.170     2-OH--C.sub.6 H.sub.4 --CH.sub.2                                    A.171     3-OH--C.sub.6 H.sub.4 --CH.sub.2                                    A.172     4-OH--C.sub.6 H.sub.4 --CH.sub.2                                    A.173     2-OCH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.174     3-OCH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.175     4-OCH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.176     2,3-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                  A.177     2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                  A.178     2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                  A.179     3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                  A.180     3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3 --CH.sub.2                  A.181     3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2 --CH.sub.2                A.182     2-OC.sub.2 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                     A.183     3-OC.sub.2 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                     A.184     4-OC.sub.2 H.sub.5 --C.sub.6 H.sub.4 --CH.sub.2                     A.185     2-O-(n-C.sub.3 H.sub.7)--C.sub.6 H.sub.4 --CH.sub.2                 A.186     3-O-(n-C.sub.3 H.sub.7)--C.sub.6 H.sub.4 --CH.sub.2                 A.187     4-O-(n-C.sub.3 H.sub.7)--C.sub.6 H.sub.4 --CH.sub.2                 A.188     2-O-(i-C.sub.3 H.sub.7)--C.sub.6 H.sub.4 --CH.sub.2                 A.189     3-O-(i-C.sub.3 H.sub.7)--C.sub.6 H.sub.4 --CH.sub.2                 A.190     4-O-(i-C.sub.3 H.sub.7)--C.sub.6 H.sub.4 --CH.sub.2                 A.191     4-O-(n-C.sub.4 H.sub.9)--C.sub.6 H.sub.4 --CH.sub.2                 A.192     3-O-(t-C.sub.4 H.sub.9)--C.sub.6 H.sub.4 --CH.sub.2                 A.193     4-O-(n-C.sub.6 H.sub.13)--C.sub.6 H.sub.4 --CH.sub.2                A.194     2-O-allyl-C.sub.6 H.sub.4 --CH.sub.2                                A.195     3-O-allyl-C.sub.6 H.sub.4 --CH.sub.2                                A.196     4-O-allyl-C.sub.6 H.sub.4 --CH.sub.2                                A.197     2-CF.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                             A.198     3-CF.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                             A.199     4-CF.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                             A.200     2-acetyl-C.sub.6 H.sub.4 --CH.sub.2                                 A.201     3-acetyl-C.sub.6 H.sub.4 --CH.sub.2                                 A.202     4-acetyl-C.sub.6 H.sub.4 --CH.sub.2                                 A.203     2-methoxycarbonyl-C.sub.6 H.sub.4 --CH.sub.2                        A.204     3-methoxycarbonyl-C.sub.6 H.sub.4 --CH.sub.2                        A.205     4-methoxycarbonyl-C.sub.6 H.sub.4 --CH.sub.2                        A.206     2-aminocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                          A.207     3-aminocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                          A.208     4-aminocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                          A.209     2-dimethylaminocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                  A.210     3-dimethylaminocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                  A.211     4-dimethylaminocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                  A.212     2-(N-methylaminocarbonyl)-C.sub.6 H.sub.4 --CH.sub.2                A.213     3-(N-methylaminocarbonyl)-C.sub.6 H.sub.4 --CH.sub.2                A.214     4-(N-methylaminocarbonyl)-C.sub.6 H.sub.4 --CH.sub.2                A.215     2-H.sub.2 N--C.sub.6 H.sub.4 --CH.sub.2                             A.216     3-H.sub.2 N--C.sub.6 H.sub.4 --CH.sub.2                             A.217     4-H.sub.2 N--C.sub.6 H.sub.4 --CH.sub.2                             A.218     2-aminothiocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                      A.219     3-aminothiocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                      A.220     4-aminothiocarbonyl-C.sub.6 H.sub.4 --CH.sub.2                      A.221     2-methoxyiminomethyl-C.sub.6 H.sub.4 --CH.sub.2                     A.222     3-methoxyiminomethyl-C.sub.6 H.sub.4 --CH.sub.2                     A.223     4-methoxyiminomethyl-C.sub.6 H.sub.4 --CH.sub.2                     A.224     2-formyl-C.sub.6 H.sub.4 --CH.sub.2                                 A.225     3-formyl-C.sub.6 H.sub.4 --CH.sub.2                                 A.226     4-formyl-C.sub.6 H.sub.4 --CH.sub.2                                 A.227     2-(1'-methoxyiminoeth-1'-yl)-C.sub.6 H.sub.4 --CH.sub.2             A.228     3-(1'-methoxyiminoeth-1'-yl)-C.sub.6 H.sub.4 --CH.sub.2             A.229     4-(1'-methoxyiminoeth-1'-yl)-C.sub.6 H.sub.4 --CH.sub.2             A.230     2-SCH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.231     3-SCH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.232     4-SCH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.233     2-SO.sub.2 CH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                    A.234     3-SO.sub.2 CH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                    A.235     4-SO.sub.2 CH.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                    A.236     2-OCF.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.237     3-OCF.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.238     4-OCF.sub.3 --C.sub.6 H.sub.4 --CH.sub.2                            A.239     2-OCHF.sub.2 --C.sub.6 H.sub.4 --CH.sub.2                           A.240     3-OCHF.sub.2 --C.sub.6 H.sub.4 --CH.sub.2                           A.241     4-OCHF.sub.2 --C.sub.6 H.sub.4 --CH.sub.2                           A.242     3-CF.sub.3, 4-OCF.sub.3 --C.sub.6 H.sub.3 --CH.sub.2                A.243     1-naphthyl-CH.sub.2                                                 A.244     2-naphthyl-CH.sub.2                                                 A.245     2-phenoxyeth-1-yl                                                   A.246     2-(2'-chlorophenoxy)eth-1-yl                                        A.247     2-(3'-chlorophenoxy)eth-1-yl                                        A.248     2-(4'-chlorophenoxy)eth-1-yl                                        A.249     2-(3',5'-dichlorophenoxy)eth-1-yl                                   A.250     2-(2'-cyanophenoxy)eth-1-yl                                         A.251     2-(3'-cyanophenoxy)eth-1-yl                                         A.252     2-(4'-cyanophenoxy)eth-1-yl                                         A.253     2-(2'-methylphenoxy)eth-1-yl                                        A.254     2-(3'-methylphenoxy)eth-1-yl                                        A.255     2-(4'-methylphenoxy)eth-1-yl                                        A.256     2-(3'-t-butylphenoxy)eth-1-yl                                       A.257     2-(4'-t-butylphenoxy)eth-1-yl                                       A.258     2-(2'-nitrophenoxy)eth-1-yl                                         A.259     2-(3'-nitrophenoxy)eth-1-yl                                         A.260     2-(4'-nitrophenoxy)eth-1-yl                                         A.261     2-(2'-methoxyphenoxy)eth-1-yl                                       A.262     2-(3'-methoxyphenoxy)eth-1-yl                                       A.263     2-(4'-methoxyphenoxy)eth-1-yl                                       A.264     2-(2'-trifluoromethylphenoxy)eth-1-yl                               A.265     2-(3'-trifluoromethylphenoxy)eth-1-yl                               A.266     2-(4'-trifluoromethylphenoxy)eth-1-yl                               A.267     2-(2'-acetylphenoxy)eth-1-yl                                        A.268     2-(3'-acetylphenoxy)eth-1-yl                                        A.269     2-(4'-acetylphenoxy)eth-1-yl                                        A.270     2-(2'-methoxycarbonyl)eth-1-yl                                      A.271     2-(3'-methoxycarbonyl)eth-1-yl                                      A.272     2-(4'-methoxycarbonyl)eth-1-yl                                      A.273     2-(2'-dimethylaminocarbonyl)eth-1-yl                                A.274     2-(3'-dimethylaminocarbonyl)eth-1-yl                                A.275     2-(4'-dimethylaminocarbonyl)eth-1-yl                                A.276     2-(2'-aminothiocarbonyl)eth-1-yl                                    A.277     2-(3'-aminothiocarbonyl)eth-1-yl                                    A.278     2-(4'-aminothiocarbonyl)eth-1-yl                                    A.279     2-(2'-methylsulfonyl)eth-1-yl                                       A.280     2-(3'-methylsulfonyl)eth-1-yl                                       A.281     2-(4'-methylsulfonyl)eth-1-yl                                       A.282     3-phenoxyprop-1-yl                                                  A.283     3-(2'-chlorophenoxy)prop-1-yl                                       A.284     3-(3'-chlorophenoxy)prop-1-yl                                       A.285     3-(4'-chlorophenoxy)prop-1-yl                                       A.286     3-(3',5',dichlorophenoxy)prop-1-yl                                  A.287     3-(2'-cyanophenoxy)prop-1-yl                                        A.288     3-(3'-cyanophenoxy)prop-1-yl                                        A.289     3-(4'-cyanophenoxy)prop-1-yl                                        A.290     3-(2'-methylphenoxy)prop-1-yl                                       A.291     3-(3'-methylphenoxy)prop-1-yl                                       A.292     3-(4'-methylphenoxy)prop-1-yl                                       A.293     3-(2'-methoxyphenoxy)prop-1-yl                                      A.294     3-(3'-methoxyphenoxy)prop-1-yl                                      A.295     3-(4'-methoxyphenoxy)prop-1-yl                                      A.296     3-(2'-trifluoromethylphenoxy)prop-1-yl                              A.297     3-(3'-trifluoromethylphenoxy)prop-1-yl                              A.298     3-(4'-trifluoromethylphenoxy)prop-1-yl                              A.299     4-phenoxybut-1-yl                                                   A.300     2-phenyleth-1-yl                                                    A.301     2-(2'-chlorophenyl)eth-1-yl                                         A.302     2-(3'-chlorophenyl)eth-1-yl                                         A.303     2-(4'-chlorophenyl)eth-1-yl                                         A.304     2-(3',5'-dichlorophenyl)eth-1-yl                                    A.305     2-(2'-cyanophenyl)eth-1-yl                                          A.306     2-(3'-cyanophenyl)eth-1-yl                                          A.307     2-(4'-cyanophenyl)eth-1-yl                                          A.308     2-(2'-methylphenyl)eth-1-yl                                         A.309     2-(3'-methylphenyl)eth-1-yl                                         A.310     2-(4'-methylphenyl)eth-1-yl                                         A.311     2-(2'-methoxyphenyl)eth-1-yl                                        A.312     2-(3'-methoxyphenyl)eth-1-yl                                        A.313     2-(4'-methoxyphenyl)eth-1-yl                                        A.314     2-(2'-trifluoromethylphenyl)eth-1-yl                                A.315     2-(3'-trifluoromethylphenyl)eth-1-yl                                A.316     2-(4'-trifluoromethylphenyl)eth-1-yl                                A.317     3-phenylprop-1-yl                                                   A.318     3-(2'-chlorophenyl) prop-1-yl                                       A.319     3-(3'-chlorophenyl)prop-1-yl                                        A.320     3-(4'-chlorophenyl)prop-1-yl                                        A.321     3-(2'-cyanophenyl)prop-1-yl                                         A.322     3-(3'-cyanophenyl)prop-1-yl                                         A.323     3-(4'-cyanophenyl)prop-1-yl                                         A.324     3-(2'-trifluoromethylphenyl)prop-1-yl                               A.325     4-phenylbut-1-yl                                                    A.326     4-(4'-chlorophenyl)but-1-yl                                         A.327     6-(4'-chlorophenyl)hex-1-yl                                         A.328     2-pyridylmethyl                                                     A.329     3-pyridylmethyl                                                     A.330     4-pyridylmethyl                                                     A.331     4-chloropyridin-2-ylmethyl                                          A.332     5-chloropyridin-2-ylmethyl                                          A.333     6-chloropyridin-2-ylmethyl                                          A.334     5-chloropyridin-3-ylmethyl                                          A.335     6-chloropyridin-3-ylmethyl                                          A.336     2-chloropyridin-4-ylmethyl                                          A.337     2-pyrimidinylmethyl                                                 A.338     4-chloropyrimidin-2-ylmethyl                                        A.339     5-chloropyrimidin-2-ylmethyl                                        A.340     2-chloropyrimidin-4-ylmethyl                                        A.341     6-chloropyrimidin-4-ylmethyl                                        A.342     2-chloropyrimidin-5-ylmethyl                                        A.343     4-pyridazinylmethyl                                                 A.344     2-pyrazinylmethyl                                                   A.345     5-chloropyrazin-2-ylmethyl                                          A.346     6-chloropyrazin-2-ylmethyl                                          A.347     3-pyridazinylmethyl                                                 A.348     6-chloropyridazin-3-ylmethyl                                        A.349     1,3,5-triazinylmethyl                                               A.350     2-furylmethyl                                                       A.351     3-furylmethyl                                                       A.352     4-bromofur-2-ylmethyl                                               A.353     5-chlorofur-2-ylmethyl                                              A.354     2-thienylmethyl                                                     A.355     3-thienylmethyl                                                     A.356     5-methylthien-3-ylmethyl                                            A.357     5-chlorothien-2-ylmethyl                                            A.358     2-chlorothien-4-ylmethyl                                            A.359     2-pyrrolylmethyl                                                    A.360     3-pyrrolylmethyl                                                    A.361     2-oxazolylmethyl                                                    A.362     4-methyloxazol-2-ylmethyl                                           A.363     5-methyloxazol-2-ylmethyl                                           A.364     4-chlorooxazol-2-ylmethyl                                           A.365     5-chlorooxazol-2-ylmethyl                                           A.366     4-oxazolylmethyl                                                    A.367     2-methyloxazol-4-ylmethyl                                           A.368     5-methyloxazol-4-ylmethyl                                           A.369     2-chlorooxazol-4-ylmethyl                                           A.370     5-chlorooxazol-4-ylmethyl                                           A.371     5-oxazolylmethyl                                                    A.372     2-methyloxazol-5-ylmethyl                                           A.373     4-methyloxazol-5-ylmethyl                                           A.374     2-chlorooxazol-5-ylmethyl                                           A.375     4-chlorooxazol-5-ylmethyl                                           A.376     2-thiazolylmethyl                                                   A.377     4-methylthiazol-2-ylmethyl                                          A.378     5-methylthiazol-2-ylmethyl                                          A.379     4-chlorothiazol-2-ylmethyl                                          A.380     5-chlorothiazol-2-ylmethyl                                          A.381     4-thiazolylmethyl                                                   A.382     2-methylthiazol-4-ylmethyl                                          A.383     5-methylthiazol-4-ylmethyl                                          A.384     2-chlorothiazol-4-ylmethyl                                          A.385     5-chlorothiazol-4-ylmethyl                                          A.386     5-thiazolylmethyl                                                   A.387     2-methylthiazol-5-ylmethyl                                          A.388     4-methylthiazol-5-ylmethyl                                          A.389     2-chlorothiazol-5-ylmethyl                                          A.390     4-chlorothiazol-5-ylmethyl                                          A.391     3-isoxazolylmethyl                                                  A.392     4-methylisoxazol-3-ylmethyl                                         A.393     5-methylisoxazol-3-ylmethyl                                         A.394     4-chloroisoxazol-3-ylmethyl                                         A.395     5-chloroisoxazol-3-ylmethyl                                         A.396     4-isoxazolylmethyl                                                  A.397     3-methylisoxazol-4-ylmethyl                                         A.398     5-methylisoxazol-4-ylmethyl                                         A.399     3-chloroisoxazol-4-ylmethyl                                         A.400     5-chloroisoxazol-4-ylmethyl                                         A.401     5-isoxazolylmethyl                                                  A.402     3-methylisoxazol-5-ylmethyl                                         A.403     4-methylisoxazol-5-ylmethyl                                         A.404     3-chloroisoxazol-5-ylmethyl                                         A.405     4-chloroisoxazol-5-ylmethyl                                         A.406     3-isothiazolylmethyl                                                A.407     4-methylisothiazol-3-ylmethyl                                       A.408     5-methylisothiazol-3-ylmethyl                                       A.409     4-chloroisothiazol-3-ylmethyl                                       A.410     5-chloroisothiazol-3-ylmethyl                                       A.411     4-isothiazolylmethyl                                                A.412     3-methylisothiazol-4-ylmethyl                                       A.413     5-methylisothiazol-4-ylmethyl                                       A.414     3-chloroisothiazol-4-ylmethyl                                       A.415     5-chloroisothiazol-4-ylmethyl                                       A.416     5-isothiazolylmethyl                                                A.417     3-methylisothiazol-5-ylmethyl                                       A.418     4-methylisothiazol-5-ylmethyl                                       A.419     3-chloroisothiazol-5-ylmethyl                                       A.420     4-chloroisothiazol-5-ylmethyl                                       A.421     4-imidazolylmethyl                                                  A.422     1-phenylpyrazol-3-ylmethyl                                          A.423     1-methylimidazol-4-ylmethyl                                         A.424     1-phenyl-1,2,4-triazol-3-ylmethyl                                   A.425     1,2,4-oxadiazol-3-ylmethyl                                          A.426     5-chloro-1,2,4-oxadiazol-3-ylmethyl                                 A.427     5-methyl-1,2,4-oxadiazol-3-ylmethyl                                 A.428     5-trifluoromethyl-1,2,4-oxadiazol-3-ylmethyl                        A.429     1,3,4-oxadiazol-2-ylmethyl                                          A.430     5-chloro-1,3,4-oxadiazol-2-ylmethyl                                 A.431     5-methyl-1,3,4-oxadiazol-2-ylmethyl                                 A.432     5-methoxy-1,3,4-oxadiazol-2-ylmethyl                                A.433     1,2,4-thiadiazol-3-ylmethyl                                         A.434     5-chloro-1,2,4-thiadiazol-3-ylmethyl                                A.435     5-methyl-1,2,4-thiadiazol-3-ylmethyl                                A.436     1,3,4-thiadiazol-2-ylmethyl                                         A.437     5-chloro-1,3,4-thiadiazol-2-ylmethyl                                A.438     5-methyl-1,3,4-thiadiazol-2-ylmethyl                                A.439     5-cyano-1,3,4-thiadiazol-2-ylmethyl                                 A.440     2-(2'-pyridinyloxy)eth-1-yl                                         A.441     2-(3'-pyridinyloxy)eth-1-yl                                         A.442     2-(4'-pyridinyloxy)eth-1-yl                                         A.443     2-(2'-pyrimidinyloxy)eth-1-yl                                       A.444     2-(4'-pyrimidinyloxy)eth-1-yl                                       A.445     2-(5'-pyrimidinyloxy)eth-1-yl                                       A.446     2-(2'-pyrazinyloxy)eth-1-yl                                         A.447     2-(2'-pyridazinyloxy)eth-1-yl                                       A.448     2-(3'-pyridazinyloxy)eth-1-yl                                       A.449     2-(1',3',5'-triazinyloxy)eth-1-yl                                   A.450     2-(5'-methylisoxazol-3'-yloxy)eth-1-yl                              A.451     2-(5'-chloroisoxazol-3'-yloxy)eth-1-yl                              A.452     2-(2'-methoxythiazol-4'-yloxy)eth-1-yl                              A.453     2-(4'-chlorooxazol-2'-yloxy)eth-l-yl                                A.454     2-(1'-phenyl-1'H-1',2',4'-triazol-3'-yloxy)eth-1-yl                 A.455     2-(1'-phenylpyrazol-3'-yloxy)eth-1-yl                               A.456     C.sub.6 H.sub.5                                                     A.457     2-Cl--C.sub.6 H.sub.4                                               A.458     3-Cl--C.sub.6 H.sub.4                                               A.459     4-Cl--C.sub.6 H.sub.4                                               A.460     2,3-Cl.sub.2 --C.sub.6 H.sub.3                                      A.461     2,4-Cl.sub.2 --C.sub.6 H.sub.3                                      A.462     2,5-Cl.sub.2 --C.sub.6 H.sub.3                                      A.463     3,4-Cl.sub.2 --C.sub.6 H.sub.3                                      A.464     3,5-Cl.sub.2 --C.sub.6 H.sub.3                                      A.465     4-CN--C.sub.6 H.sub.4                                               A.466     2-NO.sub.2 --C.sub.6 H.sub.4                                        A.467     3-NO.sub.2 --C.sub.6 H.sub.4                                        A.468     4-NO.sub.2 --C.sub.6 H.sub.4                                        A.469     2,4-(NO.sub.2).sub.2 --C.sub.6 H.sub.3                              A.470     2-CH.sub.3 --C.sub.6 H.sub.4                                        A.471     3-CH.sub.3 --C.sub.6 H.sub.4                                        A.472     4-CH.sub.3 --C.sub.6 H.sub.4                                        A.473     2,3-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                              A.474     2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                              A.475     2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                              A.476     2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                              A.477     2-C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                 A.478     3-C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                 A.479     4-C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                 A.480     3-OCH.sub.3 --C.sub.6 H.sub.4                                       A.481     4-OCH.sub.3 --C.sub.6 H.sub.4                                       A.482     3-acetyl-C.sub.6 H.sub.4                                            A.483     4-acetyl-C.sub.6 H.sub.4                                            A.484     3-methoxycarbonyl-C.sub.6 H.sub.4                                   A.485     4-methoxycarbonyl-C.sub.6 H.sub.4                                   A.486     3-CF.sub.3 --C.sub.6 H.sub.4                                        A.487     4-CF.sub.3 --C.sub.6 H.sub.4                                        A.488     2-naphthyl                                                          A.489     6-chloropyridazin-3-yl                                              A.490     5-chloropyrazin-2-yl                                                A.491     quinolin-2-yl                                                       A.492     2,5-dimethylpyrazin-3-yl                                            A.493     pyrazin-2-yl                                                        A.494     3-chloropyrid-2-yl                                                  A.495     6-chloropyrid-2-yl                                                  A.496     4-trifluoromethyl, 6-chloropyrid-2-yl                               A.497     4-trifluoromethylpyrid-2-yl                                         A.498     6-trifluoromethylpyrid-2-yl                                         A.499     6-methoxypyrid-2-yl                                                 A.500     5-chloropyrid-2-yl                                                  A.501     pyrid-2-yl                                                          A.502     benzothiazol-2-yl                                                   A.503     7-chloroquinolin-4-yl                                               A.504     3-nitropyrid-2-yl                                                   A.505     pyrrol-3-yl                                                         A.506     pyrrol-2-yl                                                         A.507     2,6-dioctylpyrid-4-yl                                               A.508     5-nitropyrid-2-yl                                                   A.509     pyrid-4-yl                                                          A.510     pyrid-3-yl                                                          A.511     pyrimidin-2-yl                                                      A.512     pyrimidin-4-yl                                                      A.513     quinazolin-4-yl                                                     A.514     6-chloropyrimidin-4-yl                                              A.515     6-methoxypyrimidin-4-yl                                             A.516     2,5,6-trichloropyrimidin-4-yl                                       A.517     2,6-dimethylpyrimidin-4-yl                                          A.518     2-methyl, 6-chloropyrimidin-4-yl                                    A.519     2-methyl, 6-ethoxypyrimidin-4-yl                                    A.520     4,5,6-trichloropyrimidin-2-yl                                       A.521     4,6-dimethoxypyrimidin-2-yl                                         A.522     4,6-dimethylpyrimidin-2-yl                                          A.523     4,6-dichloropyrimidin-2-yl                                          A.524     4-methyl, 6-methoxypyrimidin-2-yl                                   A.525     4-chloro, 6-methoxypyrimidin-2-yl                                   A.526     6-chloroquinoxalin-2-yl                                             A.527     3,6-dichloro-1,2,4-triazin-5-yl                                     A.528     4-methoxy-1,3,5-triazin-2-yl                                        A.529     4-ethoxy-1,3,5-triazin-2-yl                                         A.530     4-6-dichloro-1,3,5-triazin-2-yl                                     A.531     4-ethoxy, 6-chloro-1,3,5-triazin-2-yl                               A.532     isoxazol-3-yl                                                       A.533     thien-2-yl                                                          A.534     fur-2-yl                                                            A.535     thiatriazol-5-yl                                                    A.536     (E)-1-chloropropen-3-yl                                             A.537     (E)-4-(4'-chlorophenyl)but-2-en-1-yl                                A.538     propyn-3-yl                                                         A.539     methylcarbonyl                                                      A.540     ethylcarbonyl                                                       A.541     n-propylcarbonyl                                                    A.542     i-propylcarbonyl                                                    A.543     n-butylcarbonyl                                                     A.544     s-butylcarbonyl                                                     A.545     i-butylcarbonyl                                                     A.546     t-butylcarbonyl                                                     A.547     n-pentylcarbonyl                                                    A.548     i-pentylcarbonyl                                                    A.549     neo-pentylcarbonyl                                                  A.550     n-hexylcarbonyl                                                     A.551     n-octylcarbonyl                                                     A.552     1-propenylcarbonyl                                                  A.553     2-penten-1-ylcarbonyl                                               A.554     2,5-heptadien-1-ylcarbonyl                                          A.555     benzoyl                                                             A.556     2-chlorobenzoyl                                                     A.557     3-chlorobenzoyl                                                     A.558     4-chlorobenzoyl                                                     A.559     2-cyanobenzoyl                                                      A.560     3-cyanobenzoyl                                                      A.561     4-cyanobenzoyl                                                      A.562     4-methoxybenzoyl                                                    A.563     2-pyridylcarbonyl                                                   A.564     3-pyridylcarbonyl                                                   A.565     4-pyridylcarbonyl                                                   A.566     2-pyrimidinylcarbonyl                                               A.567     2-oxazolylcarbonyl                                                  A.568     4-methylisoxazol-5-ylcarbonyl                                       A.569     methylsulfonyl                                                      A.570     ethylsulfonyl                                                       A.571     n-propylsulfonyl                                                    A.572     i-propylsulfonyl                                                    A.573     n-butylsulfonyl                                                     A.574     t-butylsulfonyl                                                     A.575     n-pentylsulfonyl                                                    A.576     neo-pentylsulfonyl                                                  A.577     n-hexylsulfonyl                                                     A.578     n-octylsulfonyl                                                     A.579     phenylsulfonyl                                                      A.580     2-chlorophenylsulfonyl                                              A.581     3-chlorophenylsulfonyl                                              A.582     4-chlorophenylsulfonyl                                              A.583     2-cyanophenylsulfonyl                                               A.584     3-cyanophenylsulfonyl                                               A.585     4-cyanophenylsulfonyl                                               A.586     2-pyridylsulfonyl                                                   A.587     3-pyridylsulfonyl                                                   A.588     4-pyridylsulfonyl                                                   A.589     2-pyrimidinylsulfonyl                                               A.590     4-oxazolylsulfonyl                                                  A.591     5-chlorothiazol-2-ylsulfonyl                                        A.592     2-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4 --CH.sub.2                    A.593     3-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4 --CH.sub.2                    A.594     4-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4 --CH.sub.2                    A.595     2-(4'-chlorothiazol-2'-yloxy)eth-1-yl                               A.596     2-(1'-methylpyrazol-4'-yloxy)eth-1-yl                               A.597     4-Br--C.sub.6 H.sub.4                                               A.598     3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                              A.599     4-C.sub.2 H.sub.5 --C.sub.6 H.sub.4                                 A.600     3-dimethylaminocarbonyl-C.sub.6 H.sub.4                             A.601     4-dimethylaminocarbonyl-C.sub.6 H.sub.4                             A.602     2-hydroxyprop-1-yl                                                  A.603     6-hydroxy-2-methylpyrimidin-4-ylmethyl                              A.604     [6-OH, 2-CH(CH.sub.3).sub.2 -pyrimidin-4-yl]--CH.sub.2              A.605     [6-OH, 2-CH(CH.sub.2).sub.2 -pyrimidin-4-yl]--CH.sub.2              A.606     5-(2'-furan)-pent-1-yl                                              A.607     5-(2'-N-methylpyrrole)-pent-1-yl                                    A.608     [2-(4-Cl--C.sub.6 H.sub.4)-oxazol-4-yl]--CH.sub.2                   A.609     3-CF.sub.3 -pyridin-2-yl                                            A.610     5-CF.sub.3 -pyridin-2-yl                                            A.611     6-(2'-thienyl)hex-1-yl                                              ______________________________________                                    

The compounds I are suitable as fungicides.

The compounds I are distinguished by an outstanding activity against abroad spectrum of phytopathogenic fungi, in particular from the classesAscomycetes, Phycomycetes and Basidiomycetes. Some of them actsystemically and can be employed in crop protection as foliar- andsoil-acting fungicides.

They are especially important for controlling a large number of fungi ona variety of crop plants such as wheat, rye, barley, oats, rice, corn,grass, cotton, soya beans, coffee, sugar cane, grapevines, fruitspecies, ornamentals and vegetables such as cucumbers, beans andcucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plantdiseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphecichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaeraleucotricha on apples, Uncinula necator on grape-vines, Puccinia specieson cereals, Rhizoctonia species on cotton, rice and lawns, Ustilagospecies on cereals and sugar cane, Venturia inaequalis (scab) on apples,Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytiscinerea (gray mold) on strawberries, vegetables and ornamentals,grapevines, Cercospora arachidicola on peanuts, Pseudocercosporellaherpotrichoides on wheat, barley, Pyricularia oryzae on rice,Phytophthora infestans on potatoes and tomatoes, Fusarium andVerticillium species on a variety of plants, Plasmopara viticola ongrapevines, Alternaria species on vegetables and fruit.

Moreover, the compounds I are suitable for controlling harmful fungi inthe protection of materials eg. wood, paper, fibers or fabrics) and inthe protection of stored products.

The compounds I are used by treating the fungi, or the plants, seeds,materials or soil to be protected against fungal infection, with afungicidally active amount of the active ingredients. They are usedbefore or after infection of the materials, plants or seeds by thefungi.

They can be converted into the customary formulations, such assolutions, emulsions, suspensions, dusts, powders, pastes and granules.The use form depends in each case on the intended purpose; in any case,it should guarantee fine and uniform distribution of the compoundsaccording to the invention. The formulations are prepared in a knownmanner, eg. by extending the active ingredient with solvents and/orcarriers, if desired using emulsifiers and dispersants, it also beingpossible for other organic solvents to be used as auxiliary solvents ifwater is used as the diluent. Suitable auxiliaries are essentially:solvents such as aromatics, (eg. xylene), chlorinated aromatics (eg.chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg.methanol, butanol), ketones (eg. cyclohexanone), amines(eg.ethanolamine, dimethylformamide) and water; carriers such as groundnatural minerals (eg. kaolins, clays, talc, chalk) and ground syntheticminerals (eg. highly-disperse silica, silicates); emulsifiers such asnon-ionic and anionic emulsifiers (eg. polyoxyethylene fatty alcoholethers, alkylsulfonates and arylsulfonates), and dispersants such aslignine-sulfite waste liquors and methylcellulose.

In general, the fungicidal compositions comprise from 0.1 to 95,preferably from 0.5 to 90%, by weight of active ingredient.

When used in crop protection, the rates of application are from 0.01 to2.0 kg of active ingredient per ha, depending on the nature of thedesired effect.

In the treatment of seed, amounts of active ingredient of from 0.001 to0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram ofseed.

When used in the protection of materials or stored products, the rate ofapplication of active ingredient depends on the field of application andthe desired effect. Usual rates of application in the protection ofmaterials are, for example, from 0.001 g to 2 kg, preferably 0.005 g to1 kg, of active ingredient per cubic meter of material treated.

In the use form as fungicides, the agents according to the invention mayalso be present together with other active ingredients, eg. withherbicides, insecticides, growth regulators, fungicides or elsefertilizers.

A mixture of fungicides frequently results in a widened fungicidalspectrum of action.

The following list of fungicides together with which the compoundsaccording to the invention can be used is intended to illustrate thepossible combinations, but not to impose any limitation: sulfur,dithiocarbamate and their derivatives, such as iron(III)dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),ammonia complex of zinc (N,N'-propylenebisdithiocarbamate),zinc-(N,N'-propylenebisdithiocarbamate),N,N'-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives, such as dinitro-(1-methylheptyl)phenyl crotonate,2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, di-isopropyl5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate,5-amino-1-[bis(dimethylamino)-phosphinyl]-3-phenyl-1,2,4-triazole,2,3-dicyano-1,4-dithioanthraquinone,2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl1-(butylcarbamoyl)-2-benzimidazolecarbamate,2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)benzimidazole,2-(4-thiazolyl)benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloromethylthiotetrahydrophthalimide,N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfamide,5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,2-thiocyanatothiobenzothiazole, 1,4-dichloro-2, 5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,pyridine-2-thiol-1-oxide, 8-hydroxyquinoline and its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine-4,4-dioxide,2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide,2,4,5-trimethylfuran-3-carboxanilide,2,5-dimethylfuran-3-carboxycyclohexylamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine2,2,2-trichloroethyl acetal,piperazine-1,4-diylbis(2,2,2-trichloroethyl)formamide,1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,2,6-dimethyl-N-tridecyl-morpholine and its salts,2,6-dimethyl-N-cyclododecylmorpholine and its salts,N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethyl-morph oline,N-[3-(p-tert-butylphenyl)- 2-methylpropyl]piperidine, 1- [2-(2,4-dichlorophenyl)-4- ethyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole,1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-but anone,1-(4-chlorophenoxy)-3,3-dimethyl-l-(1H-1,2,4-triazol-1-yl)-2-butanol,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl) -3-pyridinemethanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

and a variety of fungicides such as dodecylguanidine acetate,3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyllglutarimide,hexachlorobenzene, methylN-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate,DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanine methyl ester,N-(2,6-dimethylphenyl)-N-chloroacetyl-D, L-2-aminobutyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,5-methyl-5-vinyl-3- (3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-[3,5-dichlorophenyl-5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione,3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano-[N-(ethylaminocarbonyl)-2-methoximino] acetamide,1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2, 6-dinitro-4-trifluoromethylphenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)-methylsilyl)methyl)1H-1,2,4-triazole;

strobilurins such as methylE-methoxyimino-[α-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-[2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methylE-methoxyimino-[α-(2-phenoxyphenyl)]acetamide, methylE-methoxyimino-[α-(2, 5-dimethylphenoxy) -o-tolyl]acetamide;

anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl) aniline,N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline,N-(4-methyl-6-cyclopropylpyrimidin-2-yl) aniline;

phenylpyrroles such as4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile;

cinnamamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloylmorpholine.

The compounds of the formula I are furthermore suitable for effectivelycontrolling animal pests from the classes of the insects, arachnids andnematodes. They can be employed as pesticides in crop protection and inthe hygiene, stored-product and veterinary sector.

The harmful insects include from the order of the lepidopterans(Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabamaargillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographagamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana,Cheimatobia brumata, Choristoneura fumiferana, Choristoneuraoccidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini,Diaphania nitidalis, Diatraea grandiosella, Earias insulana,Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana,Feltia subterranea, Galleria mellonella, Grapholitha funebrana,Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothiszea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeutamalinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygmaexigua, Leucopta coffeella, Leucoptera scitella, Lithocolletisblancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar,Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestrabrassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea,Pectinophora gossypiella, Peridroma saucia, Phalera bucephala,Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae,Plathypena scabra, Plutella xylostella, Pseudoplusia includens,Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella,Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis,Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana,Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilussinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallussolstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum,Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchusrufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassidanebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis,Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus,Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata,Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis,Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis,Hypera postica, Ips typographus, Lema bilineata, Lema melanopus,Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrusoryzophilus, Melanotus communis, Meligethes aeneus, Melolonthahippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchussulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotretachrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotretanemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus,Sitophilus granaria.

From the order of the dipterans (Diptera), for example, Aedes aegypti,Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitiscapitata, ChrysoMya bezziana, ChrysoMya hominivorax, ChrysoMyamacellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culexpipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fanniacanicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobiairritans, Haplodiplosis equestris, HyleMyia platura, Hypoderma lineata,LirioMyza sativae, LirioMyza trifolii, Lucilia caprina, Lucilia cuprina,Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Muscadomestica, Muscina stabulans, Oestrus ovis, Oscinella frit, PegoMyahysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata,Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipulaoleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniellafusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothripscitri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterans (Hymenoptera), for example, Athaliarosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta,Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata,Solenopsis invicta.

From the order of the hepteropterans (Heteroptera), for example,Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercuscingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistusimpictiventris, Leptoglossus phyllopus, Lygus lineolaris: Lyguspratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyantaperditor.

From the order of homopterans (Homoptera), for example, Acyrthosiphononobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphispomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae,Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphisradicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphumavenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae,Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvatalugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli,Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphummaidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneuralanuginosa, Trialeurodes vaporariorum, Viteus vitifolii.

From the order of the termites (Isoptera), for example, Calotermesflavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termesnatalensis.

From the order of the orthopterans (Orthoptera), for example, Achetadomestica, Blatta orientalis, Blattella germanica, Forficulaauricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplusbivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplussanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplanetaamericana, Schistocerca americana, Schistocerca peregrina, Stauronotusmaroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example, arachnids (Acarina),such as Amblyomma americanum, Amblyomma variegatum, Argas persicus,Boophilus annulatus, Boophilus decoloratus, Boophilus microplus,Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum,Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodesricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini,Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus,Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus,Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius,Tetranychus urticae.

From the class of the nematodes, for example, root-knot nematodes, eg.Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica,cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae,Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stemeelworms and foliar nematodes, eg. Belonolaimus longicaudatus,Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchusmulticinctus, Longidorus elongatus, Radopholus similis, Rotylenchusrobustus, Trichodorus primitivus, Tylenchorhynchus claytoni,Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans,Pratylenchus curvitatus, Pratylenchus goodeyi.

The active ingredients can be used as such, in the form of theirformulations or the use forms prepared therefrom, eg. in the form ofdirectly sprayable solutions, powders, suspensions or dispersions,emulsions, oil dispersions, pastes, dusts, materials for spreading, orgranules, by means of spraying, atomizing, dusting, spreading orpouring. The use forms depend entirely on the intended purposes; in anycase, they should guarantee the finest possible distribution of theactive ingredients according to the invention.

The active ingredient concentrations in the ready-to-use preparationscan be varied within substantial ranges.

In general, they are between 0.0001 and 10%, preferably between 0.01 and1%.

The active ingredients can also be used successfully in theultra-low-volume method (ULV), it being possible to apply formulationscomprising over 95% by weight of active ingredient, or even the activeingredient without additives.

The rate of application of active ingredient for controlling pests isfrom 0.1 to 2.0, preferably 0.2 to 1.0 kg/ha under field conditions.

Substances which are suitable for preparing directly sprayablesolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point, such as kerosene or dieseloil, furthermore cold tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof wetting agents, tackifier, dispersant or emulsifier. Alternatively,it is possible to prepare concentrates composed of active ingredient,wetting agent, tackifier, dispersant or emulsifier and, if desired,solvent or oil, and these concentrates are suitable for dilution withwater.

Suitable surfactants are alkali metal, alkaline earth metal and ammoniumsalts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonicacid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids andtheir alkali metal and alkaline earth metal salts, salts of sulfatedfatty alcohol glycol ether, condensates of sulfonated naphthalene andnaphthalene derivatives with formaldehyde, condensates of naphthalene,or of naphthalenesulfonic acid with phenol and formaldehyde,polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol,octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensate, ethoxylated castor oil,polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, laurylalcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite wasteliquors and methylcellulose.

Powders, materials for spreading or dusts can be prepared by mixing orjointly grinding the active ingredients with a solid carrier.

In general, the formulations comprise between 0.01 and 95% by weight,preferably between 0.1 and 90% by weight, of the active ingredient. Theactive ingredients are employed in a purity of from 90 to 100%,preferably 95% to 100% (according to NMR-spectrum).

The following are exemplary formulations:

I. 5 parts by weight of a compound according to the invention are mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dust which comprises 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention aremixed intimately with a mixture of 92 parts by weight of pulverulentsilica gel and 8 parts by weight of paraffin oil which had been sprayedonto the surface of the silica gel. This gives a formulation of theactive ingredient with good adhesion (comprises 23% by weight of activeingredient).

III. 10 parts by weight of a compound according to the invention aredissolved in a mixture composed of 90 parts by weight of xylene, 6 partsby weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol ofoleic acid N-monoethanolamide, 2 parts by weight of calciumdodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol ofethylene oxide to 1 mol of castor oil (comprises 9% by weight of activeingredient).

IV. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 60 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mol of castor oil(comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 7 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill (comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention aremixed with 10 parts by weight of N-methyl-α-pyrrolidone, which gives asolution which is suitable for use in the form of microdrops (comprises90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 40 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.Pouring the solution into 100 000 parts by weight of water and finelydistributing it therein gives an aqueous dispersion which comprises0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention aremixed thoroughly with 3 parts by weight sodiumdiisobutylnaphthalene-α-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill. Finely distributing the mixture in 20000 parts by weight of watergive the spray mixture which comprises 0.1% by weight of activeingredient.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Examples of solid carriers are mineral earths, such assilicas, silica gels, silcates, talc, kaolin, attaclay, limestone, lime,chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, eg. ammonium sulfate, ammonium phosphate, ammonium nitrate,ureas and products of vegetable origin, such as cereal meal, tree barkmeal, wood meal and nutshell meal, cellulose powders and other solidcarriers.

Various types of oils, or herbicides, fungicides, other pesticides orbactericides can be admixed with the active ingredients, if desired alsoonly just before use (tank mix). These agents can be admixed with theagents according to the invention in a weight ratio of from 1:10 to10:1.

SYNTHESIS EXAMPLES

The protocols given in the synthesis examples below were used forobtaining other compounds I by altering the starting materials asrequired. The resulting compounds are given in the table below togetherwith physical data.

Example 1 MethylE-2-methoxyimino-2-[(2-[2-(benzyloximinoeth-1'-yl)-pyrimidin-4-yl)]oxymethyl)phenyl]acetate(Compound No. I.38) ##STR36## Stage 1:4-Hydroxy-2-(benzyloximinoeth-1'-yl)pyrimidine ##STR37## 2.6 g of4-hydroxy-2-acetylpyrimidine hydrochloride, 3 g of 20% strength aqueoussodium hydroxide solution and 2.16 g of benzyloxyamine hydrochloridewere introduced into 35 ml of methanol, and the mixture was brought topH 5 using 10% strength aqueous HCl. It was then stirred for four hoursat 40° C. and then for 14 hours at room temperature. The reactionmixture was concentrated. The crude product which remained was taken upin methyl tert-butyl ether. The combined organic phases were washed withwater and dried. The mixture was reconcentrated. The crude product whichremained was purified on silica gel using ethyl acetate. This gave 2.6 gof 4-hydroxy-2-(benzyloximinoeth-1'-yl)pyrimidine as a pale yellow solid(m.p.: 142-143° C.).

Stage 2: Title compound

1.82 g of 4-Hydroxy-2-(benzyloximinoeth-1'-yl)pyrimidine, 2.15 g ofmethyl E-2-methoxyimino-2-[2-(bromomethyl)phenyl]acetate and 1.55 g ofpotassium carbonate were stirred in 30 ml of dimethylformamide for 4hours at 50° C. and then for 14 hours at room temperature. The reactionmixture was treated with water and subsequently extracted using methyltert-butyl ether. The combined organic phases were washed with water,dried over sodium sulfate and reconcentrated. The crude product whichremained was purified on silica get using cyclohexane/methyl tert-butylether 1:1. This gave 1.7 g of the title compound as a pale resin.

IR (cm-⁻¹): 1728, 1567, 1440, 1323, 1288, 1220, 1069, 1046, 1019, 986.

Example 2N-Methyl-E-2-methoxyimino-2-[(2-[(2-(benzyloximinoeth-1'-yl)-pyrimidin-4-yl)]oxymethyl)phenyl]-acetamide(Compound No. I.39) ##STR38## 4.4 g of the methyl ester (title compoundof Example 1) were dissolved in 80 ml of tetrahydrofuran and treatedwith 3.0 g of 40% strength aqueous methyl amine solution. The mixturewas stirred for 5 hours at 45° C. When cold, the reaction mixture wasconcentrated. The residue which remained was taken up in 100 ml ofmethyl tert-butyl ether. The organic phase was washed with water, driedover sodium sulfate and subsequently evaporated to dryness. 4.3 g of thetitle compound remained as a colorless solid (m.p.: 83-84° C.). Example3 MethylE-2-methoxyimino-2-[(2-[2-ethyl-6-(methoximinoeth-1'-yl)-pyrimidin-4-yl)]oxymethyl)phenyl]acetate(Compound No. I.1) ##STR39## Stage 1: Ethyl3-(2-methyl-1,3-dioxolan-2-yl)-3-oxopropionate ##STR40## 236 g ofpotassium tert-butylate were suspended in 1.3 l of diethyl carbonate andthe suspension was heated at 60° C. At this temperature, 1 mol of2-methyl-2-acetyl-1,3-dioxolane, dissolved in 500 ml of diethylcarbonate, was added dropwise in the course of three hours. Stirring wascontinued for three hours at 60° C. When cold, the mixture was pouredinto 2 l of 10%- strength sulfuric acid, the organic phase was separatedoff and the aqueous phase was extracted using ethyl acetate. Drying ofthe combined organic phases and evaporation of the diethyl carbonategave, as the residue, the crude product which was purified bydistillation in vacuo. This gave the product in a yield of 65 % (b.p.:69-72° C./0.08 mbar).

Stage 2: 4-Hydroxy-2-ethyl-6-(2-methyl-1,3-dioxolan-2-yl)pyrimidine##STR41## 54.3 g of propionamidine hydrochloride were dissolved in 350ml ethanol. 90 g of 30% strength sodium methanolate solution were addeddropwise in the course of 30 minutes and the mixture was stirred for 15minutes. 101 g of the product of stage 1 were then added dropwise in thecourse of one hour. The mixture was refluxed for eight hours andstirring was then continued for 14 hours. The reaction mixture wasconcentrated. The residue which remained was dissolved in 320 ml of 10%strength sodium hydroxide solution and then washed three times using ineach case 150 ml of methyl tert-butyl ether. The aqueous phase wasbrought to pH 5 with hydrochloric acid. The product, which as a result,precipitated was filtered off and dried. This gave 47,6 g of the productas a colorless solid (m.p.: 117-120° C.).

Stage 3: 4-Hydroxy-2-ethyl-6-acetylpyrimidine ##STR42## 20 g of thepyrimidine of Stage 2 were introduced into 200 ml dioxane. 100 ml of 5Nhydrochloric acid were added dropwise at room temperature. The mixturewas refluxed for three hours. When cold, the reaction mixture was pouredonto ice, neutralized using dilute sodium hydroxide solution, saturatedwith sodium chloride and extracted using ethyl acetate. The combinedorganic phases were dried. Evaporation of the solvent gave, as theresidue, the product as a colorless solid (m.p.: 153-155° C.).

Stage 4: MethylE-2-methoxyimino-2-[(2-[2-ethyl-6-acetyl-pyrimidin-4-yl)]oxymethyl)phenyl]acetate##STR43## 7 g of the pyrimidine from Stage 3, 12 g of methylE-2-methoxyimino-2-[2-(bromomethyl)phenyl]acetate and 10 g of potassiumcarbonate were stirred for 8 hours at 60° C. in 250 ml ofdimethylformamide. The reaction mixture was filtered. The residue whichremained after concentration of the filtrate was dissolved in ethylacetate. This organic phase was washed with dilute sodium hydroxidesolution and then with water, dried over sodium sulfate andreconcentrated. The crude product which remained was employed in Stage 5without further purification.

Stage 5: Title compound

2 g of the product of Stage 4 and 0.5 g of methoxyamine hydrochloridewere refluxed for 6 hours in 100 ml of methanol. When cold, the mixturewas filtered. The residue which remained after the filtrate had beenconcentrated was dissolved in ethyl acetate. This organic phase waswashed with water, dried over sodium sulfate and reconcentrated. Thecrude product which remained was purified on silica gel usingheptane/ethyl acetate 8:2. This gave 1 g of the title compound as acolorless solid.(m.p.: 90-92° C.).

Example 4N-Methyl-E-2-methoxyimino-2-[(2-[2-ethyl-6-(methoximinoeth-1'-yl)pyrimidin-4-yl)]oxymethyl)phenyl]acetamide(Compound No. I.23) ##STR44## 0.3 g of the methyl ester (title compoundof Example 3) was dissolved in 100 ml of tetrahydrofuran and treatedwith 50 ml of 40% strength aqueous methyl amine solution. The mixturewas stirred for 8 hours at 40° C. When cold, the batch was concentrated.The residue which remained was taken up in 100 ml of methyl tert-butylether. The organic phase was washed with water, dried over sodiumsulfate and subsequently evaporated to dryness. 0.3 g of the titlecompound remained as a pale resin.

                                      TABLE                                       __________________________________________________________________________                                                         I                         ##STR45##                                                                    No.                                                                              R.sup.1 R.sup.2                                                                          R.sup.3                                                                         n # R.sup.4                                                                              R.sup.5.sub.y                                                                    Q          Physical Data.sup.a                  __________________________________________________________________________    I.1                                                                              CH.sub.3                                                                              CH.sub.3                                                                         H 1 6 2-CH.sub.2 CH.sub.3                                                                  H  C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                      90-92                                I.2                                                                               CH.sub.2 CH.sub.3                                                                       H    61.sub.3                                                                       2-CH.sub.2 CH.sub.3                                                                     C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                      resin                I.3                                                                               (CH.sub.2).sub.2 CH.sub.3                                                               H CH.sub.3                                                                         61                                                                             2-CH.sub.2 CH.sub.3                                                                     C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                     resin                 I.4                                                                               CH.sub.3                                                                                H    61 CH.sub.3                                                                    2-CH.sub.2 CH.sub.3                                                                     C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                   resin                  I.5                                                                              CH.sub.2 CH.sub.3                                                                        H    61.sub.3                                                                       2-CH.sub.2 CH.sub.3                                                                     C (CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                resin                    I.6                                                                               (CH.sub.2).sub.2 CH.sub.3                                                               H CH.sub.3                                                                         61                                                                             2-CH.sub.2 CH.sub.3                                                                     C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                   resin                  I.7                                                                              CH.sub.2 CH═CH.sub.2                                                                 H CH.sub.3                                                                         61                                                                             2-CH.sub.2 CH.sub.3                                                                     C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.8                                                                               (CH.sub.2).sub.3 CH.sub.3                                                               H CH.sub.3                                                                         61                                                                             2-CH.sub.2 CH.sub.3                                                                     C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                   resin                  I.9                                                                               CH.sub.2 CH.sub.3                                                                       H    61.sub.3                                                                       2-CH.sub.3                                                                              C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                    103-106                I.10                                                                             (CH.sub.2).sub.2 CH.sub.3                                                                H CH.sub.3                                                                         61                                                                             2-CH.sub.3                                                                              C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                     resin                 I.11                                                                             CH.sub.3                                                                                 H    61  CH.sub.3                                                                   2-(CH.sub.2).sub.2 CH.sub.3                                                            H                                                                              C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                     resin                 I.12                                                                             CH.sub.2 CH.sub.3                                                                        H    61H.sub.3                                                                      2-(CH.sub.2).sub.2 CH.sub.3                                                            H                                                                              C(CO.sub.2 CH.sub.3) ═NOCH.sub.3                                                                    resin                 I.13                                                                             (CH.sub.2).sub.2 CH.sub.3                                                                H CH.sub.3                                                                         61                                                                             2-(CH.sub.2).sub.2 CH.sub.3                                                            H                                                                              C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                     resin                 I.14                                                                             CH.sub.2 CH═CH.sub.2                                                                 CH.sub.3                                                                       H                                                                               1                                                                                6                                                                             2-(CH.sub.2).sub.2 CH.sub.3                                                           H C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                   resin                   I.15                                                                             CH.sub.3                                                                                  H    CH.sub.3                                                                   1                                                                                6                                                                             2-CH.sub.3                                                                              C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.16                                                                             CH.sub.2 CH.sub.3                                                                         H CH.sub.3                                                                      1                                                                                6                                                                             2-CH.sub.3                                                                              C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.17                                                                             CH.sub.3                                                                                  H    CH.sub.3                                                                   1                                                                                6                                                                             2-(CH.sub.2).sub.2 CH.sub.3                                                           H C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.18                                                                             CH.sub.2 CH.sub.3                                                                         H CH.sub.3                                                                      1                                                                                6                                                                             2-(CH.sub.2).sub.2 CH.sub.3                                                           H C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.19                                                                             (CH.sub.2).sub.2 CH.sub.3                                                               CH.sub.3                                                                        H                                                                               1                                                                                6                                                                             2-(CH.sub.2).sub.2 CH.sub.3                                                           H C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.20                                                                             CH.sub.2 CH═CH.sub.2                                                                 CH.sub.3                                                                       H                                                                               1                                                                                6                                                                             2-(CH.sub.2).sub.2 CH.sub.3                                                           H C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.21                                                                             (CH.sub.2).sub.3 CH.sub.3                                                               CH.sub.3                                                                        H                                                                               1                                                                                6                                                                             2-(CH.sub.2).sub.2 CH.sub.3                                                           H C(CO.sub.2 CH.sub.3)═CHOCH.sub.3                                                                 resin                    I.22                                                                             CH.sub.3                                                                                  H    CH.sub.3                                                                   1                                                                                6                                                                             2-CH.sub.3                                                                              C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                   resin                   I.23                                                                             CH.sub.3                                                                                  H    CH.sub.3                                                                   1                                                                                6                                                                             2-CH.sub.2 CH.sub.3                                                                     C(CONHCH.sub.3)═NOCH.sub.3                                                                       resin                    I.24                                                                             CH.sub.2 CH.sub.3                                                                         H CH.sub.3                                                                      1                                                                                6                                                                             2-CH.sub.3                                                                              C(CONHCH.sub.3)═NOCH.sub.3                                                                       resin                    I.25                                                                             CH.sub.3                                                                                  H    CH.sub.3                                                                   1                                                                                2                                                                             H         C(CONHCH.sub.3)═NOCH.sub.3                                                           1670, 1568, 1527, 1461, 1441,                                                         1324, 1290, 1048, 979        I.26                                                                             CH.sub.2 CH.sub.3                                                                         H CH.sub.3                                                                      1                                                                                2                                                                             H         C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                   67-68                   I.27                                                                             CH.sub.2 CH.sub.3                                                                         H CH.sub.3                                                                      1                                                                                2                                                                             H         C(CONHCH.sub.3)═NOCH.sub.3                                                           1671, 1568, 1527, 1441, 1323                                                          1292, 1091, 1047, 1000,                                               980                                  I.28                                                                             (CH.sub.2).sub.2 CH.sub.3                                                               CH.sub.3                                                                        H                                                                               1                                                                                2                                                                             H         C(CO2CH.sub.3)═NOCH.sub.3                                                             1728, 1567, 1440, 1323, 1288,                                                                 1220, 1069,                                                  1047, 1020, 985                      I.29                                                                             (CH.sub.2).sub.2 CH.sub.3                                                               CH.sub.3                                                                        H                                                                               1                                                                                2                                                                             H         C(CONHCH.sub.3)═NOCH.sub.3                                                           1672, 1568, 1526, 1441, 1324,                                                                  1291, 1038,                                                  1004, 980                            I.30                                                                             CH(CH.sub.3).sub.2                                                                        HH.sub.3                                                                        1                                                                                2                                                                             H         C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                                   78-80                   I.31                                                                             CH(CH.sub.3).sub.2                                                                        HCH.sub.3                                                                        1                                                                               2                                                                             H          C(CONHCH.sub.3)═NOCH.sub.3                                                                        100-102                I.32                                                                             (CH.sub.2).sub.3 CH.sub.3                                                                 HH.sub.3                                                                         1                                                                               2                                                                             H          C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                       1729, 1567, 1440, 1323, 1287                                                                 1220, 1069,                                                  1045, 1020, 985                      I.33                                                                             (CH.sub.2).sub.3 CH.sub.3                                                                 HH.sub.3                                                                         1                                                                               2                                                                             H          C(CONHCH.sub.3)═NOCH.sub.3                                                           1671, 1568, 1527, 1440, 1324,                                                            1291, 1037, 979          I.34                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                        H                                                                                1                                                                               2                                                                             H          C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                       1729, 1567, 1462, 1440, 1323,                                                               1288, 1220,                                                   1079, 1039, 1021                     I.35                                                                             CH.sub.2 CH(CH.sub.3).sub.2                                                             CH.sub.3                                                                       H   1                                                                               2                                                                             H          C(CONHCH.sub.3)═NOCH.sub.3                                                           1671, 1568, 1527, 1462, 1440,                                                                1324, 1292,                                                   1038, 979                            I.36                                                                             CH(CH.sub.3)CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                          H                                                                                1                                                                               2                                                                             H          C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                       1729, 1566, 1461, 1440, 1322,                                                              1287, 1220, 1070,                                              1017, 986                            I.37                                                                             CH(CH.sub.3)CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                          H                                                                                1                                                                               2                                                                             H          C(CONHCH.sub.3)═NOCH.sub.3                                                                         98-100                I.38                                                                             CH.sub.2 --C.sub.6 H.sub.5                                                                HCH.sub.3                                                                        1                                                                               2                                                                             H          C(CO.sub.2 CH.sub.3)═NOCH.sub.3                                                       1728, 1567, 1440, 1323, 1288,                                                             1220, 1069, 1046,                                               1019, 986                            I.39                                                                             CH.sub.2 --C.sub.6 H.sub.5                                                                HCH.sub.3                                                                        1                                                                               2                                                                             H          C(CONHCH.sub.3)═NOCH.sub.3                                                                        83-84                  __________________________________________________________________________     .sup.a : m.p. (° C.); IR (cm.sup.-1); .sup.1 H NMR (δ in ppm

Examples of the activity against harmful fungi

The fungicidal activity of the compounds of the general formula I wasdemonstrated by the following experiments:

The active ingredients were formulated as a 20% strength emulsion in amixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN(Lutensol® AP6, wetting agent having emulsifying and dispersant actionbased on the ethoxylated alkylphenols) and 10% by weight of Emulphor® EL(Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and dilutedwith water to give the desired concentration.

Activity against Plasmopara viticola (downy mildew of grapevine)

Grapevines in pots (cultivar: "Muller Thurgau") were sprayed to drippoint with the preparation of the active ingredient (rate ofapplication: 250 ppm). After 8 days, the plants were sprayed with zoospore suspension of the fungus Plasmopara viticola and left to stand for5 days at 20-30° C. and high atmospheric humidity. Prior to assessment,the plants were then left to stand at high atmospheric humidity for 16hours. Evaluation was carried out visually.

In this test, the disease level of the plants which had been treatedwith the compounds 1, 3, 5, 7, 11, 14, 17, 18, 20, 22, 25, 26, 27, 28,29, 30, 31, 32, 33, 34, 35, 36, 37, 38 and 39 according to the inventionwas 15%, while the untreated (control) plants showed a disease level of80%.

Examples of the activity against animal pests

The activity of the compounds of the general formula I against animalpests was demonstrated by the following experiments:

The active ingredients were formulated

a. as a 0.1% strength solution in acetone or

b. as a 10% strength emulsion in a mixture of 70% by weight ofcyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wettingagent having emulsifying and dispersant action based on the ethoxylatedalkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifierbased on ethoxylated fatty alcohols) and diluted to give the desiredconcentration, using acetone in the case of a. and water in the case ofb.

After conclusion of the experiments, the lowest concentration wasdetermined in each case at which the compounds still caused an 80 to100% inhibition or mortality in comparison to untreated controls (limitor minimal concentration).

What is claimed is:
 1. A pyrimidyl phenyl or pyrimidyl benzyl ether ofthe formula I ##STR46## or a salt or N-oxide thereof, where thesubstituents and indices have the following meanings:Q is C(CO₂CH₃)═CHCH₃, C(CO₂ CH₃)═CHOCH₃, C(CO₂ CH₃)═NOCH₃, C(CONHCH₃)═NOCH₃ orN(OCH₃)--CO₂ CH₃ ; n is 0 or 1; R¹ is C₁ -C₆ -alkyl or aryl-C₁ -C₂-alkyl, it being possible for the aryl radical to be partially or fullyhalogenated and/or to carry one to three of the following groups:C₁ -C₄-alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy; R² is hydrogen, C₁ -C₆-alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl. C₃ -C₆ -cycloalkyl or aryl: R³is hydrogen, halogen, C₁ -C₄ -alkyl or C₁ -C₂ -haloalkyl; R⁴ ishydrogen, halogen, C₁ -C₂ -alkyl, C₁ -C₂ -alkoxy, cyano or nitro: y is0, 1, 2 or 3, it being possible for the radicals R⁵ to be different if yis 2 or 3; R⁵ is cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl or C₁-C₄ -alkoxy.
 2. A process for the preparation of a compound I as definedin claim 1, which comprises converting a pyrimidine derivative of theformula IIa ##STR47## where L¹ is a nucleophilically exchangeableleaving group with a phenol or a benzyl alcohol of the formula IIIa##STR48## in an inert solvent to give the corresponding ether of theformula IVa ##STR49## and subsequently reacting IVa with anO-substituted hydroxylamine (R¹ --O--NH₂) or a salt thereof to give I.3. A composition which is suitable for controlling pests or harmfulfungi, comprising a solid or liquid carrier and a compound of theformula I as claimed in claim
 1. 4. A method for controlling harmfulfungi, which comprises treating the fungi, or the materials, plants, thesoil or seed to be protected against fungal attack, with an effectiveamount of a compound of the formula I as desired in claim
 1. 5. A methodfor controlling pests, which comprises treating the pests, or thematerials, plants, the soil or seed to be protected against them, withan effective amount of a compound of the defined formula I as claimed inclaim
 1. 6. A pyrimidyl phenyl or pyrimidal benzyl ether as claimed inclaim 1 wherein Q in formula I is C(COOCH₃)═CHOCH₃.
 7. A pyrimidylphenyl or pyrimidal benzyl ether as claimed in claim 1 wherein Q informula I is C(COOCH₃)═NOCH₃ or C(CONHCH₃)═NOCH₃.